Organic electroluminescent materials and devices

ABSTRACT

A composition including a first compound capable of functioning as a phosphorescent emitter in an OLED is provided. The first compound has at least one aromatic ring and at least one substituent R directly bonded to one of the at least one aromatic rings. Each substituent R has the formula of 
                         
where (a) G 1  is selected from NR 1 , SiR 1 R 2 , GeR 1 R 2 , alkyl, cycloalkyl, and combinations thereof; and G 2  is a non-aromatic polycyclic group; (b) G 1  is a direct bond; and G 2  is a non-aromatic spiro polycyclic group; or (c) G 1  is selected from direct bond, NR 1 , SiR 1 R 2 , GeR 1 R 2 , alkyl, cycloalkyl, and combinations thereof; G 2  is a non-aromatic polycyclic group; and R is directly bonded to a phenyl, pyridine, or triazine. R 1 , R 2 , and R 3  are a variety of substituents. Formulations and devices, such as an OLEDs, that include the first compound are also described.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims priority to U.S. Provisional application No. 62/213,757 filed Sep. 3, 2015; U.S. Provisional application No. 62/232,194 filed Sep. 24, 2015; U.S. Provisional application No. 62/291,960 filed Feb. 5, 2016; U.S. Provisional application No. 62/322,510 filed Apr. 14, 2016; and U.S. Provisional application No. 62/330,412 filed May 2, 2016, the entire contents of which is incorporated herein by reference.

PARTIES TO A JOINT RESEARCH AGREEMENT

The claimed invention was made by, on behalf of, and/or in connection with one or more of the following parties to a joint university corporation research agreement: The Regents of the University of Michigan, Princeton University, University of Southern California, and the Universal Display Corporation. The agreement was in effect on and before the date the claimed invention was made, and the claimed invention was made as a result of activities undertaken within the scope of the agreement.

FIELD

The present invention relates to compounds for use as emitters, and devices, such as organic light emitting diodes, including the same.

BACKGROUND

Opto-electronic devices that make use of organic materials are becoming increasingly desirable for a number of reasons. Many of the materials used to make such devices are relatively inexpensive, so organic opto-electronic devices have the potential for cost advantages over inorganic devices. In addition, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications such as fabrication on a flexible substrate. Examples of organic opto-electronic devices include organic light emitting diodes/devices (OLEDs), organic phototransistors, organic photovoltaic cells, and organic photodetectors. For OLEDs, the organic materials may have performance advantages over conventional materials. For example, the wavelength at which an organic emissive layer emits light may generally be readily tuned with appropriate dopants.

OLEDs make use of thin organic films that emit light when voltage is applied across the device. OLEDs are becoming an increasingly interesting technology for use in applications such as flat panel displays, illumination, and backlighting. Several OLED materials and configurations are described in U.S. Pat. Nos. 5,844,363, 6,303,238, and 5,707,745, which are incorporated herein by reference in their entirety.

One application for phosphorescent emissive molecules is a full color display. Industry standards for such a display call for pixels adapted to emit particular colors, referred to as “saturated” colors. In particular, these standards call for saturated red, green, and blue pixels. Alternatively the OLED can be designed to emit white light. In conventional liquid crystal displays emission from a white backlight is filtered using absorption filters to produce red, green and blue emission. The same technique can also be used with OLEDs. The white OLED can be either a single EML device or a stack structure. Color may be measured using CIE coordinates, which are well known to the art.

One example of a green emissive molecule is tris(2-phenylpyridine) iridium, denoted Ir(ppy)₃, which has the following structure:

In this, and later figures herein, we depict the dative bond from nitrogen to metal (here, Ir) as a straight line.

As used herein, the term “organic” includes polymeric materials as well as small molecule organic materials that may be used to fabricate organic opto-electronic devices. “Small molecule” refers to any organic material that is not a polymer, and “small molecules” may actually be quite large. Small molecules may include repeat units in some circumstances. For example, using a long chain alkyl group as a substituent does not remove a molecule from the “small molecule” class. Small molecules may also be incorporated into polymers, for example as a pendent group on a polymer backbone or as a part of the backbone. Small molecules may also serve as the core moiety of a dendrimer, which consists of a series of chemical shells built on the core moiety. The core moiety of a dendrimer may be a fluorescent or phosphorescent small molecule emitter. A dendrimer may be a “small molecule,” and it is believed that all dendrimers currently used in the field of OLEDs are small molecules.

As used herein, “top” means furthest away from the substrate, while “bottom” means closest to the substrate. Where a first layer is described as “disposed over” a second layer, the first layer is disposed further away from substrate. There may be other layers between the first and second layer, unless it is specified that the first layer is “in contact with” the second layer. For example, a cathode may be described as “disposed over” an anode, even though there are various organic layers in between.

As used herein, “solution processible” means capable of being dissolved, dispersed, or transported in and/or deposited from a liquid medium, either in solution or suspension form.

A ligand may be referred to as “photoactive” when it is believed that the ligand directly contributes to the photoactive properties of an emissive material. A ligand may be referred to as “ancillary” when it is believed that the ligand does not contribute to the photoactive properties of an emissive material, although an ancillary ligand may alter the properties of a photoactive ligand.

As used herein, and as would be generally understood by one skilled in the art, a first “Highest Occupied Molecular Orbital” (HOMO) or “Lowest Unoccupied Molecular Orbital” (LUMO) energy level is “greater than” or “higher than” a second HOMO or LUMO energy level if the first energy level is closer to the vacuum energy level. Since ionization potentials (IP) are measured as a negative energy relative to a vacuum level, a higher HOMO energy level corresponds to an IP having a smaller absolute value (an IP that is less negative). Similarly, a higher LUMO energy level corresponds to an electron affinity (EA) having a smaller absolute value (an EA that is less negative). On a conventional energy level diagram, with the vacuum level at the top, the LUMO energy level of a material is higher than the HOMO energy level of the same material. A “higher” HOMO or LUMO energy level appears closer to the top of such a diagram than a “lower” HOMO or LUMO energy level.

As used herein, and as would be generally understood by one skilled in the art, a first work function is “greater than” or “higher than” a second work function if the first work function has a higher absolute value. Because work functions are generally measured as negative numbers relative to vacuum level, this means that a “higher” work function is more negative. On a conventional energy level diagram, with the vacuum level at the top, a “higher” work function is illustrated as further away from the vacuum level in the downward direction. Thus, the definitions of HOMO and LUMO energy levels follow a different convention than work functions.

More details on OLEDs, and the definitions described above, can be found in U.S. Pat. No. 7,279,704, which is incorporated herein by reference in its entirety.

SUMMARY

According to one embodiment, a composition comprising a first compound is provided. In the composition, the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature, and the first compound has at least one aromatic ring and at least one substituent R, where each of the at least one substituent R is directly bonded to one of the at least one aromatic rings. Each of the at least one substituent R has the formula of

where:

-   -   (a) G¹ is selected from the group consisting of NR¹, SiR¹R²,         GeR¹R², alkyl, cycloalkyl, and combinations thereof; and G² is a         non-aromatic polycyclic group, which can be further substituted         by one or more R³;     -   (b) G¹ is a direct bond; and G² is a non-aromatic spiro         polycyclic group, which can be further substituted by one or         more R³; or     -   (c) G¹ is selected from the group consisting of: direct bond,         NR¹, SiR¹R², GeR¹R², alkyl, cycloalkyl, and combinations         thereof; G² is a non-aromatic polycyclic group, which can be         further substituted by one or more R³; and R is directly bonded         to an aromatic ring selected from the group consisting of         phenyl, pyridine, and triazine, which can be further fused to         other rings;

R¹, R², and R³ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

each G¹ and G² is independently, optionally, partially or fully deuterated.

According to another embodiment, an organic light emitting diode/device (OLED) is also provided. The OLED can include an anode, a cathode, and an organic layer, disposed between the anode and the cathode. The organic layer can include the first compound as described herein. According to yet another embodiment, the organic light emitting device is incorporated into one or more device selected from a consumer product, an electronic component module, and/or a lighting panel.

According to yet another embodiment, a formulation containing the first compound as described herein is provided.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows an organic light emitting device.

FIG. 2 shows an inverted organic light emitting device that does not have a separate electron transport layer.

DETAILED DESCRIPTION

Generally, an OLED comprises at least one organic layer disposed between and electrically connected to an anode and a cathode. When a current is applied, the anode injects holes and the cathode injects electrons into the organic layer(s). The injected holes and electrons each migrate toward the oppositely charged electrode. When an electron and hole localize on the same molecule, an “exciton,” which is a localized electron-hole pair having an excited energy state, is formed. Light is emitted when the exciton relaxes via a photoemissive mechanism. In some cases, the exciton may be localized on an excimer or an exciplex. Non-radiative mechanisms, such as thermal relaxation, may also occur, but are generally considered undesirable.

The initial OLEDs used emissive molecules that emitted light from their singlet states (“fluorescence”) as disclosed, for example, in U.S. Pat. No. 4,769,292, which is incorporated by reference in its entirety. Fluorescent emission generally occurs in a time frame of less than 10 nanoseconds.

More recently, OLEDs having emissive materials that emit light from triplet states (“phosphorescence”) have been demonstrated. Baldo et al., “Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,” Nature, vol. 395, 151-154, 1998; (“Baldo-I”) and Baldo et al., “Very high-efficiency green organic light-emitting devices based on electrophosphorescence,” Appl. Phys. Lett., vol. 75, No. 3, 4-6 (1999) (“Baldo-II”), are incorporated by reference in their entireties. Phosphorescence is described in more detail in U.S. Pat. No. 7,279,704 at cols. 5-6, which are incorporated by reference.

FIG. 1 shows an organic light emitting device 100. The figures are not necessarily drawn to scale. Device 100 may include a substrate 110, an anode 115, a hole injection layer 120, a hole transport layer 125, an electron blocking layer 130, an emissive layer 135, a hole blocking layer 140, an electron transport layer 145, an electron injection layer 150, a protective layer 155, a cathode 160, and a barrier layer 170. Cathode 160 is a compound cathode having a first conductive layer 162 and a second conductive layer 164. Device 100 may be fabricated by depositing the layers described, in order. The properties and functions of these various layers, as well as example materials, are described in more detail in U.S. Pat. No. 7,279,704 at cols. 6-10, which are incorporated by reference.

More examples for each of these layers are available. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F₄-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of emissive and host materials are disclosed in U.S. Pat. No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003/0230980, which is incorporated by reference in its entirety. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entireties, disclose examples of cathodes including compound cathodes having a thin layer of metal such as Mg:Ag with an overlying transparent, electrically-conductive, sputter-deposited ITO layer. The theory and use of blocking layers is described in more detail in U.S. Pat. No. 6,097,147 and U.S. Patent Application Publication No. 2003/0230980, which are incorporated by reference in their entireties. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of protective layers may be found in U.S. Patent Application Publication No. 2004/0174116, which is incorporated by reference in its entirety.

FIG. 2 shows an inverted OLED 200. The device includes a substrate 210, a cathode 215, an emissive layer 220, a hole transport layer 225, and an anode 230. Device 200 may be fabricated by depositing the layers described, in order. Because the most common OLED configuration has a cathode disposed over the anode, and device 200 has cathode 215 disposed under anode 230, device 200 may be referred to as an “inverted” OLED. Materials similar to those described with respect to device 100 may be used in the corresponding layers of device 200. FIG. 2 provides one example of how some layers may be omitted from the structure of device 100.

The simple layered structure illustrated in FIGS. 1 and 2 is provided by way of non-limiting example, and it is understood that embodiments of the invention may be used in connection with a wide variety of other structures. The specific materials and structures described are exemplary in nature, and other materials and structures may be used. Functional OLEDs may be achieved by combining the various layers described in different ways, or layers may be omitted entirely, based on design, performance, and cost factors. Other layers not specifically described may also be included. Materials other than those specifically described may be used. Although many of the examples provided herein describe various layers as comprising a single material, it is understood that combinations of materials, such as a mixture of host and dopant, or more generally a mixture, may be used. Also, the layers may have various sublayers. The names given to the various layers herein are not intended to be strictly limiting. For example, in device 200, hole transport layer 225 transports holes and injects holes into emissive layer 220, and may be described as a hole transport layer or a hole injection layer. In one embodiment, an OLED may be described as having an “organic layer” disposed between a cathode and an anode. This organic layer may comprise a single layer, or may further comprise multiple layers of different organic materials as described, for example, with respect to FIGS. 1 and 2.

Structures and materials not specifically described may also be used, such as OLEDs comprised of polymeric materials (PLEDs) such as disclosed in U.S. Pat. No. 5,247,190 to Friend et al., which is incorporated by reference in its entirety. By way of further example, OLEDs having a single organic layer may be used. OLEDs may be stacked, for example as described in U.S. Pat. No. 5,707,745 to Forrest et al, which is incorporated by reference in its entirety. The OLED structure may deviate from the simple layered structure illustrated in FIGS. 1 and 2. For example, the substrate may include an angled reflective surface to improve out-coupling, such as a mesa structure as described in U.S. Pat. No. 6,091,195 to Forrest et al., and/or a pit structure as described in U.S. Pat. No. 5,834,893 to Bulovic et al., which are incorporated by reference in their entireties.

Unless otherwise specified, any of the layers of the various embodiments may be deposited by any suitable method. For the organic layers, preferred methods include thermal evaporation, ink-jet, such as described in U.S. Pat. Nos. 6,013,982 and 6,087,196, which are incorporated by reference in their entireties, organic vapor phase deposition (OVPD), such as described in U.S. Pat. No. 6,337,102 to Forrest et al., which is incorporated by reference in its entirety, and deposition by organic vapor jet printing (OVJP), such as described in U.S. Pat. No. 7,431,968, which is incorporated by reference in its entirety. Other suitable deposition methods include spin coating and other solution based processes. Solution based processes are preferably carried out in nitrogen or an inert atmosphere. For the other layers, preferred methods include thermal evaporation. Preferred patterning methods include deposition through a mask, cold welding such as described in U.S. Pat. Nos. 6,294,398 and 6,468,819, which are incorporated by reference in their entireties, and patterning associated with some of the deposition methods such as ink-jet and OVJD. Other methods may also be used. The materials to be deposited may be modified to make them compatible with a particular deposition method. For example, substituents such as alkyl and aryl groups, branched or unbranched, and preferably containing at least 3 carbons, may be used in small molecules to enhance their ability to undergo solution processing. Substituents having 20 carbons or more may be used, and 3-20 carbons is a preferred range. Materials with asymmetric structures may have better solution processibility than those having symmetric structures, because asymmetric materials may have a lower tendency to recrystallize. Dendrimer substituents may be used to enhance the ability of small molecules to undergo solution processing.

Devices fabricated in accordance with embodiments of the present invention may further optionally comprise a barrier layer. One purpose of the barrier layer is to protect the electrodes and organic layers from damaging exposure to harmful species in the environment including moisture, vapor and/or gases, etc. The barrier layer may be deposited over, under or next to a substrate, an electrode, or over any other parts of a device including an edge. The barrier layer may comprise a single layer, or multiple layers. The barrier layer may be formed by various known chemical vapor deposition techniques and may include compositions having a single phase as well as compositions having multiple phases. Any suitable material or combination of materials may be used for the barrier layer. The barrier layer may incorporate an inorganic or an organic compound or both. The preferred barrier layer comprises a mixture of a polymeric material and a non-polymeric material as described in U.S. Pat. No. 7,968,146, PCT Pat. Application Nos. PCT/US2007/023098 and PCT/US2009/042829, which are herein incorporated by reference in their entireties. To be considered a “mixture”, the aforesaid polymeric and non-polymeric materials comprising the barrier layer should be deposited under the same reaction conditions and/or at the same time. The weight ratio of polymeric to non-polymeric material may be in the range of 95:5 to 5:95. The polymeric material and the non-polymeric material may be created from the same precursor material. In one example, the mixture of a polymeric material and a non-polymeric material consists essentially of polymeric silicon and inorganic silicon.

Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of electronic component modules (or units) that can be incorporated into a variety of electronic products or intermediate components. Examples of such electronic products or intermediate components include display screens, lighting devices such as discrete light source devices or lighting panels, etc. that can be utilized by the end-user product manufacturers. Such electronic component modules can optionally include the driving electronics and/or power source(s). Devices fabricated in accordance with embodiments of the invention can be incorporated into a wide variety of consumer products that have one or more of the electronic component modules (or units) incorporated therein. Such consumer products would include any kind of products that include one or more light source(s) and/or one or more of some type of visual displays. Some examples of such consumer products include flat panel displays, computer monitors, medical monitors, televisions, billboards, lights for interior or exterior illumination and/or signaling, heads-up displays, fully or partially transparent displays, flexible displays, laser printers, telephones, cell phones, tablets, phablets, personal digital assistants (PDAs), wearable device, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicles, a large area wall, theater or stadium screen, or a sign. Various control mechanisms may be used to control devices fabricated in accordance with the present invention, including passive matrix and active matrix. Many of the devices are intended for use in a temperature range comfortable to humans, such as 18 degrees C. to 30 degrees C., and more preferably at room temperature (20-25 degrees C.), but could be used outside this temperature range, for example, from −40 degree C. to +80 degree C.

The materials and structures described herein may have applications in devices other than OLEDs. For example, other optoelectronic devices such as organic solar cells and organic photodetectors may employ the materials and structures. More generally, organic devices, such as organic transistors, may employ the materials and structures.

In the field of organic chemistry, a polycyclic compound is an organic chemical featuring several closed rings of atoms, primarily carbon. These ring substructures comprises cycloalkanes, aromatics, and other ring types. They come in sizes of three atoms and upward, and in combinations of linkages that include tethering (such as in biaryls), fusing (edge-to-edge, such as in anthracene and steroids), links via a single atom (such as in spiro compounds), and bridged cyclics such as adamantane. Though “poly” literally means “many”, in this context polycyclic includes smaller rings such as bicyclic, tricyclic, and tetracyclic.

The term “halo,” “halogen,” or “halide” as used herein includes fluorine, chlorine, bromine, and iodine.

The term “alkyl” as used herein contemplates both straight and branched chain alkyl radicals. Preferred alkyl groups are those containing from one to fifteen carbon atoms and includes methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, and the like. Additionally, the alkyl group may be optionally substituted.

The term “cycloalkyl” as used herein contemplates cyclic alkyl radicals. Preferred cycloalkyl groups are those containing 3 to 10 ring carbon atoms and includes cyclopropyl, cyclopentyl, cyclohexyl, adamantyl, and the like. Additionally, the cycloalkyl group may be optionally substituted.

The term “alkenyl” as used herein contemplates both straight and branched chain alkene radicals. Preferred alkenyl groups are those containing two to fifteen carbon atoms. Additionally, the alkenyl group may be optionally substituted.

The term “alkynyl” as used herein contemplates both straight and branched chain alkyne radicals. Preferred alkynyl groups are those containing two to fifteen carbon atoms. Additionally, the alkynyl group may be optionally substituted.

The terms “aralkyl” or “arylalkyl” as used herein are used interchangeably and contemplate an alkyl group that has as a substituent an aromatic group. Additionally, the aralkyl group may be optionally substituted.

The term “heterocyclic group” as used herein contemplates aromatic and non-aromatic cyclic radicals. Hetero-aromatic cyclic radicals also means heteroaryl. Preferred hetero-non-aromatic cyclic groups are those containing 3 to 7 ring atoms which includes at least one hetero atom, and includes cyclic amines such as morpholino, piperdino, pyrrolidino, and the like, and cyclic ethers, such as tetrahydrofuran, tetrahydropyran, and the like. Additionally, the heterocyclic group may be optionally substituted.

The term “aryl” or “aromatic group” as used herein contemplates single-ring groups and polycyclic ring systems. The polycyclic rings may have two or more rings in which two carbons are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred aryl groups are those containing six to thirty carbon atoms, preferably six to twenty carbon atoms, more preferably six to twelve carbon atoms. Especially preferred is an aryl group having six carbons, ten carbons or twelve carbons. Suitable aryl groups include phenyl, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene, preferably phenyl, biphenyl, triphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group may be optionally substituted.

The term “heteroaryl” as used herein contemplates single-ring hetero-aromatic groups that may include from one to five heteroatoms. The term heteroaryl also includes polycyclic hetero-aromatic systems having two or more rings in which two atoms are common to two adjoining rings (the rings are “fused”) wherein at least one of the rings is a heteroaryl, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryl, heterocycles, and/or heteroaryls. Preferred heteroaryl groups are those containing three to thirty carbon atoms, preferably three to twenty carbon atoms, more preferably three to twelve carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborine, 1,3-azaborine, 1,4-azaborine, borazine, and aza-analogs thereof. Additionally, the heteroaryl group may be optionally substituted.

The alkyl, cycloalkyl, alkenyl, alkynyl, aralkyl, heterocyclic group, aryl, and heteroaryl may be unsubstituted or may be substituted with one or more substituents selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, cyclic amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

As used herein, “substituted” indicates that a substituent other than H is bonded to the relevant position, such as carbon. Thus, for example, where R¹ is mono-substituted, then one R¹ must be other than H. Similarly, where R¹ is di-substituted, then two of R¹ must be other than H. Similarly, where R¹ is unsubstituted, R¹ is hydrogen for all available positions.

The “aza” designation in the fragments described herein, i.e. aza-dibenzofuran, aza-dibenzothiophene, etc. means that one or more of the C—H groups in the respective fragment can be replaced by a nitrogen atom, for example, and without any limitation, azatriphenylene encompasses both dibenzo[f,h]quinoxaline and dibenzo[f,h]quinoline. One of ordinary skill in the art can readily envision other nitrogen analogs of the aza-derivatives described above, and all such analogs are intended to be encompassed by the terms as set forth herein.

It is to be understood that when a molecular fragment is described as being a substituent or otherwise attached to another moiety, its name may be written as if it were a fragment (e.g. phenyl, phenylene, naphthyl, dibenzofuryl) or as if it were the whole molecule (e.g. benzene, naphthalene, dibenzofuran). As used herein, these different ways of designating a substituent or attached fragment are considered to be equivalent.

According to one embodiment, a composition comprising a first compound is described. In the composition, the first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature, and the first compound has at least one aromatic ring and at least one substituent R, where each of the at least one substituent R is directly bonded to one of the at least one aromatic rings. Each of the at least one substituent R has the formula of

where:

-   -   (a) G¹ is selected from the group consisting of NR¹, SiR¹R²,         GeR¹R², alkyl, cycloalkyl, and combinations thereof; and G² is a         non-aromatic polycyclic group, which can be further substituted         by one or more R³;     -   (b) G¹ is a direct bond; and G² is a non-aromatic spiro         polycyclic group, which can be further substituted by one or         more R³; or     -   (c) G¹ is selected from the group consisting of: direct bond,         NR¹, SiR¹R², GeR¹R², alkyl, cycloalkyl, and combinations         thereof; G² is a non-aromatic polycyclic group, which can be         further substituted by one or more R³; and R is directly bonded         to an aromatic ring selected from the group consisting of         phenyl, pyridine, and triazine, which can be further fused to         other rings;

R¹, R², and R³ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfonyl, sulfonyl, phosphino, and combinations thereof; and

each G¹ and G² is independently, optionally, partially or fully deuterated.

In some embodiments, G¹ is SiR¹R². In some embodiments, G¹ is NR¹. In some embodiments, G¹ is alkyl. In some such embodiments, G¹ is selected from the group consisting of divalent methyl, ethyl, propyl, and butyl. In some embodiments, G¹ is fully or partially deuterated.

In some embodiments, G² is polycyclic alkyl. In some embodiments, G² is carborane. In some embodiments, G² contains at least one heteroatom. In some embodiments, G² includes at least one heterocyclic group.

In some embodiments, the first compound is capable of emitting light from a triplet excited state to a ground singlet state at room temperature.

In some embodiments, the first compound is a metal coordination complex having a metal-carbon bond. In some such embodiments, the metal is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu. In some such embodiments, the metal is Ir, while the metal is Pt is other embodiments.

In some embodiments, the first compound has the formula of M(L¹)_(x)(L²)_(y)(L³)_(z), where:

L¹, L² and L³ can be the same or different;

x is 1, 2, or 3;

y is 0, 1, or 2;

z is 0, 1, or 2;

x+y+z is the oxidation state of the metal M;

L¹, L² and L³ are each independently selected from the group consisting of:

each X¹ to X¹⁷ are independently selected from the group consisting of carbon and nitrogen;

X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO₂, CR′R″, SiR′R″, and GeR′R″;

each R′ and R″ is independently, optionally fused or joined to form a ring:

each R_(a), R_(b), R_(c), and R_(d) independently represents from mono substitution to the maximum possible number of substitutions, or no substitution;

each R′, R″, R_(a), R_(b), R_(c), and R_(d) is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;

any two adjacent substitutents of R_(a), R_(b), R_(c), and R_(d) are optionally fused or joined to form a ring or form a multidentate ligand; and

at least one of the R_(a), R_(b), R_(c), and R_(d) includes the at least one substituent R.

In some embodiments where the first compound has the structure M(L¹)_(x)(L²)_(y)(L³)_(z), the first compound has the formula of Ir(L¹)₂(L²). In some such embodiments, L¹ has the formula selected from the group consisting of:

and L² has the formula

In some such embodiments, L² has the formula:

where:

R_(e), R_(f), R_(h) and R_(i) are independently selected from group consisting of alkyl, cycloalkyl, aryl, and heteroaryl;

at least one of R_(e), R_(f), R_(h), and R_(i) has at least two carbon atoms; and

R_(g) is selected from group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In some embodiments where the first compound has the formula of Ir(L¹)₂(L²), ligands L¹ and L² are different and each independently selected from the group consisting of:

In some embodiments where the first compound has the formula of Ir(L¹)₂(L²), ligands L¹ and L² are each independently selected from the group consisting of:

In some embodiments where the first compound has the structure M(L¹)_(x)(L²)_(y)(L³)_(z), the first compound has the formula of Pt(L¹)₂ or Pt(L¹)(L²). In some embodiments where the first compound has the formula of Pt(L¹)₂ or Pt(L¹)(L²), one L¹ is connected to the other L¹ or L² to form a tetradentate ligand.

In some embodiments where the first compound has the structure M(L¹)_(x)(L²)_(y)(L³)_(z), at least one of R_(a), R_(b), R_(c), and R_(d) includes an alkyl or cycloalkyl group that is partially or fully deuterated.

In some embodiments, G² is selected from the group consisting of:

In some embodiments, each of the at least one substituent R is independently selected from the group consisting of:

In some embodiments where the first compound has the structure M(L¹)_(x)(L²)_(y)(L³)_(z), at least one of L¹, L², and L³ is selected from the group consisting of:

In some embodiments where the first compound has the formula of Ir(L¹)₂(L²), ligands L¹ and L² are different and each independently selected from the group consisting of:

In some embodiments where the first compound has the formula of M(L¹)_(x)(L²)_(y)(L³)_(z), ligand L¹ is L_(A) having the following structure:

selected from the group consisting of L_(A1) to L_(A2480) as listed below:

L_(Ai), i R_(A1) R_(A2) R_(A3) R_(A4) R_(A5) R_(A6) 1.

H H H H H 2.

H H H H H 3.

H H H H H 4.

H H H H H 5.

H H H H H 6.

H H H H H 7.

H H H H H 8.

H H H H H 9.

H H H H H 10.

H H H H H 11.

H H H H H 12.

H H H H H 13.

H H H H H 14.

H H H H H 15.

H H H H H 16.

H H H H H 17.

H H H H H 18.

H H H H H 19.

H H H H H 20.

H H H H H 21.

H H H H H 22.

H H H H H 23.

H H H H H 24.

H H H H H 25.

H H H H H 26.

H H H H H 27.

H H H H H 28.

H H H H H 29.

H H H H H 30.

H H H H H 31.

H H H H H 32.

H H H H H 33.

H H H H H 34.

H H H H H 35.

H H H H H 36.

H H H H H 37.

H H H H H 38.

H H H H H 39.

H H H H H 40.

H H H H H 41.

H H H H H 42.

H H H H H 43.

H H H H H 44.

H H H H H 45.

H H H H H 46.

H H H H H 47.

H H H H H 48.

H H H H H 49.

H H H H H 50.

H H H H H 51.

H H H H H 52.

H H H H H 53.

H H H H H 54.

H H H H H 55.

H H H H H 56.

H H H H H 57.

H H H H H 58.

H H H H H 59.

H H H H H 60.

H H H H H 61.

H H H H H 62.

H H H H H 63.

H H H H H 64.

H H H H H 65.

H H H H H 66.

H H H H H 67.

H H H H H 68.

H H H H H 69.

H H H H H 70.

H H H H H 71.

H H H H H 72.

H H H H H 73.

H H H H H 74.

H H H H H 75.

H H H H H 76.

H H H H H 77.

H H H H H 78.

H H H H H 79.

H H H H H 80.

H H H H H 81.

H H H H H 82.

H H H H H 83.

H H H H H 84.

H H H H H 85.

H H H H H 86.

H H H H H 87.

H H H H H 88.

H H H H H 89.

H H H H H 90.

H H H H H 91.

H H H H H 92.

H H H H H 93.

H H H H H 94.

H H H H H 95.

H H H H H 96.

H H H H H 97.

H H H H H 98.

H H H H H 99.

H H H H H 100.

H H H H H 101.

H H H H H 102.

H H H H H 103.

H H H H H 104.

H H H H H 105.

H H H H H 106.

H H H H H 107.

H H H H H 108.

H H H H H 109.

H H H H H 110.

H H H H H 111.

H H H H H 112.

H H H H H 113.

H H H H H 114.

H H H H H 115.

H H H H H 116.

H H H H H 117.

H H H H H 118.

H H H H H 119.

H H H H H 120.

H H H H H 121.

H H H H H 122.

H H H H H 123.

H H H H H 124.

H H H H H 125.

H H H H H 126.

H H H H H 127.

H H H H H 128.

H H H H H 129.

H H H H H 130.

H H H H H 131.

H H H H H 132.

H H H H H 133.

H H H H H 134.

H H H H H 135.

H H H H H 136.

H H H H H 137.

H H H H H 138.

H H H H H 139.

H H H H H 140.

H H H H H 141.

H H H H H 142.

H H H H H 143.

H H H H H 144.

H H H H H 145.

H H H H H 146.

H H H H H 147.

H H H H H 148.

H H H H H 149.

H H H H H 150.

H H H H H 151.

H H H H H 152.

H H H H H 153.

H H H H H 154.

H H H H H 155.

H H H H H 156.

H H H H H 157.

H H H H H 158.

H H H H H 159.

H H H H H 160.

H H H H H 161.

H H H H H 162.

H H H H H 163.

H H H H H 164.

H H H H H 165.

H H H H H 166.

H H H H H 167.

H H H H H 168.

H H H H H 169.

H H H H H 170.

H CD₃ H H H 171.

H CD₃ H H H 172.

H CD₃ H H H 173.

H CD₃ H H H 174.

H CD₃ H H H 175.

H CD₃ H H H 176.

H CD₃ H H H 177.

H CD₃ H H H 178.

H CD₃ H H H 179.

H CD₃ H H H 180.

H CD₃ H H H 181.

H CD₃ H H H 182.

H CD₃ H H H 183.

H CD₃ H H H 184.

H CD₃ H H H 185.

H CD₃ H H H 186.

H CD₃ H H H 187.

H CD₃ H H H 188.

H CD₃ H H H 189.

H CD₃ H H H 190.

H CD₃ H H H 191.

H CD₃ H H H 192.

H CD₃ H H H 193.

H CD₃ H H H 194.

H CD₃ H H H 195.

H CD₃ H H H 196.

H CD₃ H H H 197.

H CD₃ H H H 198.

H CD₃ H H H 199.

H CD₃ H H H 200.

H CD₃ H H H 201.

H CD₃ H H H 202.

H CD₃ H H H 203.

H CD₃ H H H 204.

H CD₃ H H H 205.

H CD₃ H H H 206.

H CD₃ H H H 207.

H CD₃ H H H 208.

H CD₃ H H H 209.

H CD₃ H H H 210.

H CD₃ H H H 211.

H CD₃ H H H 212.

H CD₃ H H H 213.

H CD₃ H H H 214.

H CD₃ H H H 215.

H CD₃ H H H 216.

H CD₃ H H H 217.

H CD₃ H H H 218.

H CD₃ H H H 219.

H CD₃ H H H 220.

H CD₃ H H H 221.

H CD₃ H H H 222.

H CD₃ H H H 223.

H CD₃ H H H 224.

H CD₃ H H H 225.

H CD₃ H H H 226.

H CD₃ H H H 227.

H CD₃ H H H 228.

H CD₃ H H H 229.

H CD₃ H H H 230.

H CD₃ H H H 231.

H CD₃ H H H 232.

H CD₃ H H H 233.

H CD₃ H H H 234.

H CD₃ H H H 235.

H CD₃ H H H 236.

H CD₃ H H H 237.

H CD₃ H H H 238.

H CD₃ H H H 239.

H CD₃ H H H 240.

H CD₃ H H H 241.

H CD₃ H H H 242.

H CD₃ H H H 243.

H CD₃ H H H 244.

H CD₃ H H H 245.

H CD₃ H H H 246.

H CD₃ H H H 247.

H CD₃ H H H 248.

H CD₃ H H H 249.

H CD₃ H H H 250.

H CD₃ H H H 251.

H CD₃ H H H 252.

H CD₃ H H H 253.

H CD₃ H H H 254.

H CD₃ H H H 255.

H CD₃ H H H 256.

H CD₃ H H H 257.

H CD₃ H H H 258.

H CD₃ H H H 259.

H CD₃ H H H 260.

H CD₃ H H H 261.

H CD₃ H H H 262.

H CD₃ H H H 263.

H CD₃ H H H 264.

H CD₃ H H H 265.

H CD₃ H H H 266.

H CD₃ H H H 267.

H CD₃ H H H 268.

H CD₃ H H H 269.

H CD₃ H H H 270.

H CD₃ H H H 271.

H CD₃ H H H 272.

H CD₃ H H H 273.

H CD₃ H H H 274.

H CD₃ H H H 275.

H CD₃ H H H 276.

H CD₃ H H H 277.

H CD₃ H H H 278.

H CD₃ H H H 279.

H CD₃ H H H 280.

H CD₃ H H H 281.

H CD₃ H H H 282.

H CD₃ H H H 283.

H CD₃ H H H 284.

H CD₃ H H H 285.

H CD₃ H H H 286.

H CD₃ H H H 287.

H CD₃ H H H 288.

H CD₃ H H H 289.

H CD₃ H H H 290.

H CD₃ H H H 291.

H CD₃ H H H 292.

H CD₃ H H H 293.

H CD₃ H H H 294.

H CD₃ H H H 295.

H CD₃ H H H 296.

H CD₃ H H H 297.

H CD₃ H H H 298.

H CD₃ H H H 299.

H CD₃ H H H 300.

H CD₃ H H H 301.

H CD₃ H H H 302.

H CD₃ H H H 303.

H CD₃ H H H 304.

H CD₃ H H H 305.

H CD₃ H H H 306.

H CD₃ H H H 307.

H CD₃ H H H 308.

H CD₃ H H H 309.

H CD₃ H H H 310.

H CD₃ H H H 311.

H CD₃ H H H 312.

H CD₃ H H H 313.

H CD₃ H H H 314.

H CD₃ H H H 315.

H CD₃ H H H 316.

H CD₃ H H H 317.

H CD₃ H H H 318.

H CD₃ H H H 319.

H CD₃ H H H 320.

H CD₃ H H H 321.

H CD₃ H H H 322.

H CD₃ H H H 323.

H CD₃ H H H 324.

H CD₃ H H H 325.

H CD₃ H H H 326.

H CD₃ H H H 327.

H CD₃ H H H 328.

H CD₃ H H H 329.

H CD₃ H H H 330.

H CD₃ H H H 331.

H CD₃ H H H 332.

H CD₃ H H H 333.

H CD₃ H H H 334.

H CD₃ H H H 335.

H CD₃ H H H 336.

H CD₃ H H H 337.

H CD₃ H H H 338.

H CD₃ H H H 339.

CD₃ CD₃ H H CD₃ 340.

CD₃ CD₃ H H CD₃ 341.

CD₃ CD₃ H H CD₃ 342.

CD₃ CD₃ H H CD₃ 343.

CD₃ CD₃ H H CD₃ 344.

CD₃ CD₃ H H CD₃ 345.

CD₃ CD₃ H H CD₃ 346.

CD₃ CD₃ H H CD₃ 347.

CD₃ CD₃ H H CD₃ 348.

CD₃ CD₃ H H CD₃ 349.

CD₃ CD₃ H H CD₃ 350.

CD₃ CD₃ H H CD₃ 351.

CD₃ CD₃ H H CD₃ 352.

CD₃ CD₃ H H CD₃ 353.

CD₃ CD₃ H H CD₃ 354.

CD₃ CD₃ H H CD₃ 355.

CD₃ CD₃ H H CD₃ 356.

CD₃ CD₃ H H CD₃ 357.

CD₃ CD₃ H H CD₃ 358.

CD₃ CD₃ H H CD₃ 359.

CD₃ CD₃ H H CD₃ 360.

CD₃ CD₃ H H CD₃ 361.

CD₃ CD₃ H H CD₃ 362.

CD₃ CD₃ H H CD₃ 363.

CD₃ CD₃ H H CD₃ 364.

CD₃ CD₃ H H CD₃ 365.

CD₃ CD₃ H H CD₃ 366.

CD₃ CD₃ H H CD₃ 367.

CD₃ CD₃ H H CD₃ 368.

CD₃ CD₃ H H CD₃ 369.

CD₃ CD₃ H H CD₃ 370.

CD₃ CD₃ H H CD₃ 371.

CD₃ CD₃ H H CD₃ 372.

CD₃ CD₃ H H CD₃ 373.

CD₃ CD₃ H H CD₃ 374.

CD₃ CD₃ H H CD₃ 375.

CD₃ CD₃ H H CD₃ 376.

CD₃ CD₃ H H CD₃ 377.

CD₃ CD₃ H H CD₃ 378.

CD₃ CD₃ H H CD₃ 379.

CD₃ CD₃ H H CD₃ 380.

CD₃ CD₃ H H CD₃ 381.

CD₃ CD₃ H H CD₃ 382.

CD₃ CD₃ H H CD₃ 383.

CD₃ CD₃ H H CD₃ 384.

CD₃ CD₃ H H CD₃ 385.

CD₃ CD₃ H H CD₃ 386.

CD₃ CD₃ H H CD₃ 387.

CD₃ CD₃ H H CD₃ 388.

CD₃ CD₃ H H CD₃ 389.

CD₃ CD₃ H H CD₃ 390.

CD₃ CD₃ H H CD₃ 391.

CD₃ CD₃ H H CD₃ 392.

CD₃ CD₃ H H CD₃ 393.

CD₃ CD₃ H H CD₃ 394.

CD₃ CD₃ H H CD₃ 395.

CD₃ CD₃ H H CD₃ 396.

CD₃ CD₃ H H CD₃ 397.

CD₃ CD₃ H H CD₃ 398.

CD₃ CD₃ H H CD₃ 399.

CD₃ CD₃ H H CD₃ 400.

CD₃ CD₃ H H CD₃ 401.

CD₃ CD₃ H H CD₃ 402.

CD₃ CD₃ H H CD₃ 403.

CD₃ CD₃ H H CD₃ 404.

CD₃ CD₃ H H CD₃ 405.

CD₃ CD₃ H H CD₃ 406.

CD₃ CD₃ H H CD₃ 407.

CD₃ CD₃ H H CD₃ 408.

CD₃ CD₃ H H CD₃ 409.

CD₃ CD₃ H H CD₃ 410.

CD₃ CD₃ H H CD₃ 411.

CD₃ CD₃ H H CD₃ 412.

CD₃ CD₃ H H CD₃ 413.

CD₃ CD₃ H H CD₃ 414.

CD₃ CD₃ H H CD₃ 415.

CD₃ CD₃ H H CD₃ 416.

CD₃ CD₃ H H CD₃ 417.

CD₃ CD₃ H H CD₃ 418.

CD₃ CD₃ H H CD₃ 419.

CD₃ CD₃ H H CD₃ 420.

CD₃ CD₃ H H CD₃ 421.

CD₃ CD₃ H H CD₃ 422.

CD₃ CD₃ H H CD₃ 423.

CD₃ CD₃ H H CD₃ 424.

CD₃ CD₃ H H CD₃ 425.

CD₃ CD₃ H H CD₃ 426.

CD₃ CD₃ H H CD₃ 427.

CD₃ CD₃ H H CD₃ 428.

CD₃ CD₃ H H CD₃ 429.

CD₃ CD₃ H H CD₃ 430.

CD₃ CD₃ H H CD₃ 431.

CD₃ CD₃ H H CD₃ 432.

CD₃ CD₃ H H CD₃ 433.

CD₃ CD₃ H H CD₃ 434.

CD₃ CD₃ H H CD₃ 435.

CD₃ CD₃ H H CD₃ 436.

CD₃ CD₃ H H CD₃ 437.

CD₃ CD₃ H H CD₃ 438.

CD₃ CD₃ H H CD₃ 439.

CD₃ CD₃ H H CD₃ 440.

CD₃ CD₃ H H CD₃ 441.

CD₃ CD₃ H H CD₃ 442.

CD₃ CD₃ H H CD₃ 443.

CD₃ CD₃ H H CD₃ 444.

CD₃ CD₃ H H CD₃ 445.

CD₃ CD₃ H H CD₃ 446.

CD₃ CD₃ H H CD₃ 447.

CD₃ CD₃ H H CD₃ 448.

CD₃ CD₃ H H CD₃ 449.

CD₃ CD₃ H H CD₃ 450.

CD₃ CD₃ H H CD₃ 451.

CD₃ CD₃ H H CD₃ 452.

CD₃ CD₃ H H CD₃ 453.

CD₃ CD₃ H H CD₃ 454.

CD₃ CD₃ H H CD₃ 455.

CD₃ CD₃ H H CD₃ 456.

CD₃ CD₃ H H CD₃ 457.

CD₃ CD₃ H H CD₃ 458.

CD₃ CD₃ H H CD₃ 459.

CD₃ CD₃ H H CD₃ 460.

CD₃ CD₃ H H CD₃ 461.

CD₃ CD₃ H H CD₃ 462.

CD₃ CD₃ H H CD₃ 463.

CD₃ CD₃ H H CD₃ 464.

CD₃ CD₃ H H CD₃ 465.

CD₃ CD₃ H H CD₃ 466.

CD₃ CD₃ H H CD₃ 467.

CD₃ CD₃ H H CD₃ 468.

CD₃ CD₃ H H CD₃ 469.

CD₃ CD₃ H H CD₃ 470.

CD₃ CD₃ H H CD₃ 471.

CD₃ CD₃ H H CD₃ 472.

CD₃ CD₃ H H CD₃ 473.

CD₃ CD₃ H H CD₃ 474.

CD₃ CD₃ H H CD₃ 475.

CD₃ CD₃ H H CD₃ 476.

CD₃ CD₃ H H CD₃ 477.

CD₃ CD₃ H H CD₃ 478.

CD₃ CD₃ H H CD₃ 479.

CD₃ CD₃ H H CD₃ 480.

CD₃ CD₃ H H CD₃ 481.

CD₃ CD₃ H H CD₃ 482.

CD₃ CD₃ H H CD₃ 483.

CD₃ CD₃ H H CD₃ 484.

CD₃ CD₃ H H CD₃ 485.

CD₃ CD₃ H H CD₃ 486.

CD₃ CD₃ H H CD₃ 487.

CD₃ CD₃ H H CD₃ 488.

CD₃ CD₃ H H CD₃ 489.

CD₃ CD₃ H H CD₃ 490.

CD₃ CD₃ H H CD₃ 491.

CD₃ CD₃ H H CD₃ 492.

CD₃ CD₃ H H CD₃ 493.

CD₃ CD₃ H H CD₃ 494.

CD₃ CD₃ H H CD₃ 495.

CD₃ CD₃ H H CD₃ 496.

CD₃ CD₃ H H CD₃ 497.

CD₃ CD₃ H H CD₃ 498.

CD₃ CD₃ H H CD₃ 499.

CD₃ CD₃ H H CD₃ 500.

CD₃ CD₃ H H CD₃ 501.

CD₃ CD₃ H H CD₃ 502.

CD₃ CD₃ H H CD₃ 503.

CD₃ CD₃ H H CD₃ 504.

CD₃ CD₃ H H CD₃ 505.

CD₃ CD₃ H H CD₃ 506.

CD₃ CD₃ H H CD₃ 507.

CD₃ CD₃ H H CD₃ 508. H

CD₃ H H H 509. H

CD₃ H H H 510. H

CD₃ H H H 511. H

CD₃ H H H 512. H

CD₃ H H H 513. H

CD₃ H H H 514. H

CD₃ H H H 515. H

CD₃ H H H 516. H

CD₃ H H H 517. H

CD₃ H H H 518. H

CD₃ H H H 519. H

CD₃ H H H 520. H

CD₃ H H H 521. H

CD₃ H H H 522. H

CD₃ H H H 523. H

CD₃ H H H 524. H

CD₃ H H H 525. H

CD₃ H H H 526. H

CD₃ H H H 527. H

CD₃ H H H 528. H

CD₃ H H H 529. H

CD₃ H H H 530. H

CD₃ H H H 531. H

CD₃ H H H 532. H

CD₃ H H H 533. H

CD₃ H H H 534. H

CD₃ H H H 535. H

CD₃ H H H 536. H

CD₃ H H H 537. H

CD₃ H H H 538. H

CD₃ H H H 539. H

CD₃ H H H 540. H

CD₃ H H H 541. H

CD₃ H H H 542. H

CD₃ H H H 543. H

CD₃ H H H 544. H

CD₃ H H H 545. H

CD₃ H H H 546. H

CD₃ H H H 547. H

CD₃ H H H 548. H

CD₃ H H H 549. H

CD₃ H H H 550. H

CD₃ H H H 551. H

CD₃ H H H 552. H

CD₃ H H H 553. H

CD₃ H H H 554. H

CD₃ H H H 555. H

CD₃ H H H 556. H

CD₃ H H H 557. H

CD₃ H H H 558. H

CD₃ H H H 559. H

CD₃ H H H 560. H

CD₃ H H H 561. H

CD₃ H H H 562. H

CD₃ H H H 563. H

CD₃ H H H 564. H

CD₃ H H H 565. H

CD₃ H H H 566. H

CD₃ H H H 567. H

CD₃ H H H 568. H

CD₃ H H H 569. H

CD₃ H H H 570. H

CD₃ H H H 571. H

CD₃ H H H 572. H

CD₃ H H H 573. H

CD₃ H H H 574. H

CD₃ H H H 575. H

CD₃ H H H 576. H

CD₃ H H H 577. H

CD₃ H H H 578. H

CD₃ H H H 579. H

CD₃ H H H 580. H

CD₃ H H H 581. H

CD₃ H H H 582. H

CD₃ H H H 583. H

CD₃ H H H 584. H

CD₃ H H H 585. H

CD₃ H H H 586. H

CD₃ H H H 587. H

CD₃ H H H 588. H

CD₃ H H H 589. H

CD₃ H H H 590. H

CD₃ H H H 591. H

CD₃ H H H 592. H

CD₃ H H H 593. H

CD₃ H H H 594. H

CD₃ H H H 595. H

CD₃ H H H 596. H

CD₃ H H H 597. H

CD₃ H H H 598. H

CD₃ H H H 599. H

CD₃ H H H 600. H

CD₃ H H H 601. H

CD₃ H H H 602. H

CD₃ H H H 603. H

CD₃ H H H 604. H

CD₃ H H H 605. H

CD₃ H H H 606. H

CD₃ H H H 607. H

CD₃ H H H 608. H

CD₃ H H H 609. H

CD₃ H H H 610. H

CD₃ H H H 611. H

CD₃ H H H 612. H

CD₃ H H H 613. H

CD₃ H H H 614. H

CD₃ H H H 615. H

CD₃ H H H 616. H

CD₃ H H H 617. H

CD₃ H H H 618. H

CD₃ H H H 619. H

CD₃ H H H 620. H

CD₃ H H H 621. H

CD₃ H H H 622. H

CD₃ H H H 623. H

CD₃ H H H 624. H

CD₃ H H H 625. H

CD₃ H H H 626. H

CD₃ H H H 627. H

CD₃ H H H 628. H

CD₃ H H H 629. H

CD₃ H H H 630. H

CD₃ H H H 631. H

CD₃ H H H 632. H

CD₃ H H H 633. H

CD₃ H H H 634. H

CD₃ H H H 635. H

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H H H 1207. CD₃ H

H H H 1208. CD₃ H

H H H 1209. CD₃ H

H H H 1210. CD₃ H

H H H 1211. CD₃ H

H H H 1212. CD₃ H

H H H 1213. CD₃ H

H H H 1214. CD₃ H

H H H 1215. CD₃ H

H H H 1216. CD₃ H

H H H 1217. CD₃ H

H H H 1218. CD₃ H

H H H 1219. CD₃ H

H H H 1220. CD₃ H

H H H 1221. CD₃ H

H H H 1222. CD₃ H

H H H 1223. CD₃ H

H H H 1224. CD₃ H

H H H 1225. CD₃ H

H H H 1226. CD₃ H

H H H 1227. CD₃ H

H H H 1228. CD₃ H

H H H 1229. CD₃ H

H H H 1230. CD₃ H

H H H 1231. CD₃ H

H H H 1232. CD₃ H

H H H 1233. CD₃ H

H H H 1234. CD₃ H

H H H 1235. CD₃ H

H H H 1236. CD₃ H

H H H 1237. CD₃ H

H H H 1238. CD₃ H

H H H 1239. CD₃ H

H H H 1240. CD₃ H

H H H 1241. CD₃ H

H H H 1242. CD₃ H

H H H 1243. CD₃ H

H H H 1244. CD₃ H

H H H 1245. CD₃ H

H H H 1246. CD₃ H

H H H 1247. CD₃ H

H H H 1248. CD₃ H

H H H 1249. CD₃ H

H H H 1250. CD₃ H

H H H 1251. CD₃ H

H H H 1252. CD₃ H

H H H 1253. CD₃ H

H H H 1254. CD₃ H

H H H 1255. CD₃ H

H H H 1256. CD₃ H

H H H 1257. CD₃ H

H H H 1258. CD₃ H

H H H 1259. CD₃ H

H H H 1260. CD₃ H

H H H 1261. CD₃ H

H H H 1262. CD₃ H

H H H 1263. CD₃ H

H H H 1264. CD₃ H

H H H 1265. CD₃ H

H H H 1266. CD₃ H

H H H 1267. CD₃ H

H H H 1268. CD₃ H

H H H 1269. CD₃ H

H H H 1270. CD₃ H

H H H 1271. CD₃ H

H H H 1272. CD₃ H

H H H 1273. CD₃ H

H H H 1274. CD₃ H

H H H 1275. CD₃ H

H H H 1276. CD₃ H

H H H 1277. CD₃ H

H H H 1278. CD₃ H

H H H 1279. CD₃ H

H H H 1280. CD₃ H

H H H 1281. CD₃ H

H H H 1282. CD₃ H

H H H 1283. CD₃ H

H H H 1284. CD₃ H

H H H 1285. CD₃ H

H H H 1286. CD₃ H

H H H 1287. CD₃ H

H H H 1288. CD₃ H

H H H 1289. CD₃ H

H H H 1290. CD₃ H

H H H 1291. CD₃ H

H H H 1292. CD₃ H

H H H 1293. CD₃ H

H H H 1294. CD₃ H

H H H 1295. CD₃ H

H H H 1296. CD₃ H

H H H 1297. CD₃ H

H H H 1298. CD₃ H

H H H 1299. CD₃ H

H H H 1300. CD₃ H

H H H 1301. CD₃ H

H H H 1302. CD₃ H

H H H 1303. CD₃ H

H H H 1304. CD₃ H

H H H 1305. CD₃ H

H H H 1306. CD₃ H

H H H 1307. CD₃ H

H H H 1308. CD₃ H

H H H 1309. CD₃ H

H H H 1310. CD₃ H

H H H 1311. CD₃ H

H H H 1312. CD₃ H

H H H 1313. CD₃ H

H H H 1314. CD₃ H

H H H 1315. CD₃ H

H H H 1316. CD₃ H

H H H 1317. CD₃ H

H H H 1318. CD₃ H

H H H 1319. CD₃ H

H H H 1320. CD₃ H

H H H 1321. CD₃ H

H H H 1322. CD₃ H

H H H 1323. CD₃ H

H H H 1324. CD₃ H

H H H 1325. CD₃ H

H H H 1326. CD₃ H

H H H 1327. CD₃ H

H H H 1328. CD₃ H

H H H 1329. CD₃ H

H H H 1330. CD₃ H

H H H 1331. CD₃ H

H H H 1332. CD₃ H

H H H 1333. CD₃ H

H H H 1334. CD₃ H

H H H 1335. CD₃ H

H H H 1336. CD₃ H

H H H 1337. CD₃ H

H H H 1338. CD₃ H

H H H 1339. CD₃ H

H H H 1340. CD₃ H

H H H 1341. CD₃ H

H H H 1342. CD₃ H

H H H 1343. CD₃ H

H H H 1344. CD₃ H

H H H 1345. CD₃ H

H H H 1346. CD₃ H

H H H 1347. CD₃ H

H H H 1348. CD₃ H

H H H 1349. CD₃ H

H H H 1350. CD₃ H

H H H 1351. CD₃ H

H H H 1352. CD₃ H

H H H 1353. H CD₃

H H H 1354. H CD₃

H H H 1355. H CD₃

H H H 1356. H CD₃

H H H 1357. H CD₃

H H H 1358. H CD₃

H H H 1359. H CD₃

H H H 1360. H CD₃

H H H 1361. H CD₃

H H H 1362. H CD₃

H H H 1363. H CD₃

H H H 1364. H CD₃

H H H 1365. H CD₃

H H H 1366. H CD₃

H H H 1367. H CD₃

H H H 1368. H CD₃

H H H 1369. H CD₃

H H H 1370. H CD₃

H H H 1371. H CD₃

H H H 1372. H CD₃

H H H 1373. H CD₃

H H H 1374. H CD₃

H H H 1375. H CD₃

H H H 1376. H CD₃

H H H 1377. H CD₃

H H H 1378. H CD₃

H H H 1379. H CD₃

H H H 1380. H CD₃

H H H 1381. H CD₃

H H H 1382. H CD₃

H H H 1383. H CD₃

H H H 1384. H CD₃

H H H 1385. H CD₃

H H H 1386. H CD₃

H H H 1387. H CD₃

H H H 1388. H CD₃

H H H 1389. H CD₃

H H H 1390. H CD₃

H H H 1391. H CD₃

H H H 1392. H CD₃

H H H 1393. H CD₃

H H H 1394. H CD₃

H H H 1395. H CD₃

H H H 1396. H CD₃

H H H 1397. H CD₃

H H H 1398. H CD₃

H H H 1399. H CD₃

H H H 1400. H CD₃

H H H 1401. H CD₃

H H H 1402. H CD₃

H H H 1403. H CD₃

H H H 1404. H CD₃

H H H 1405. H CD₃

H H H 1406. H CD₃

H H H 1407. H CD₃

H H H 1408. H CD₃

H H H 1409. H CD₃

H H H 1410. H CD₃

H H H 1411. H CD₃

H H H 1412. H CD₃

H H H 1413. H CD₃

H H H 1414. H CD₃

H H H 1415. H CD₃

H H H 1416. H CD₃

H H H 1417. H CD₃

H H H 1418. H CD₃

H H H 1419. H CD₃

H H H 1420. H CD₃

H H H 1421. H CD₃

H H H 1422. H CD₃

H H H 1423. H CD₃

H H H 1424. H CD₃

H H H 1425. H CD₃

H H H 1426. H CD₃

H H H 1427. H CD₃

H H H 1428. H CD₃

H H H 1429. H CD₃

H H H 1430. H CD₃

H H H 1431. H CD₃

H H H 1432. H CD₃

H H H 1433. H CD₃

H H H 1434. H CD₃

H H H 1435. H CD₃

H H H 1436. H CD₃

H H H 1437. H CD₃

H H H 1438. H CD₃

H H H 1439. H CD₃

H H H 1440. H CD₃

H H H 1441. H CD₃

H H H 1442. H CD₃

H H H 1443. H CD₃

H H H 1444. H CD₃

H H H 1445. H CD₃

H H H 1446. H CD₃

H H H 1447. H CD₃

H H H 1448. H CD₃

H H H 1449. H CD₃

H H H 1450. H CD₃

H H H 1451. H CD₃

H H H 1452. H CD₃

H H H 1453. H CD₃

H H H 1454. H CD₃

H H H 1455. H CD₃

H H H 1456. H CD₃

H H H 1457. H CD₃

H H H 1458. H CD₃

H H H 1459. H CD₃

H H H 1460. H CD₃

H H H 1461. H CD₃

H H H 1462. H CD₃

H H H 1463. H CD₃

H H H 1464. H CD₃

H H H 1465. H CD₃

H H H 1466. H CD₃

H H H 1467. H CD₃

H H H 1468. H CD₃

H H H 1469. H CD₃

H H H 1470. H CD₃

H H H 1471. H CD₃

H H H 1472. H CD₃

H H H 1473. H CD₃

H H H 1474. H CD₃

H H H 1475. H CD₃

H H H 1476. H CD₃

H H H 1477. H CD₃

H H H 1478. H CD₃

H H H 1479. H CD₃

H H H 1480. H CD₃

H H H 1481. H CD₃

H H H 1482. H CD₃

H H H 1483. H CD₃

H H H 1484. H CD₃

H H H 1485. H CD₃

H H H 1486. H CD₃

H H H 1487. H CD₃

H H H 1488. H CD₃

H H H 1489. H CD₃

H H H 1490. H CD₃

H H H 1491. H CD₃

H H H 1492. H CD₃

H H H 1493. H CD₃

H H H 1494. H CD₃

H H H 1495. H CD₃

H H H 1496. H CD₃

H H H 1497. H CD₃

H H H 1498. H CD₃

H H H 1499. H CD₃

H H H 1500. H CD₃

H H H 1501. H CD₃

H H H 1502. H CD₃

H H H 1503. H CD₃

H H H 1504. H CD₃

H H H 1505. H CD₃

H H H 1506. H CD₃

H H H 1507. H CD₃

H H H 1508. H CD₃

H H H 1509. H CD₃

H H H 1510. H CD₃

H H H 1511. H CD₃

H H H 1512. H CD₃

H H H 1513. H CD₃

H H H 1514. H CD₃

H H H 1515. H CD₃

H H H 1516. H CD₃

H H H 1517. H CD₃

H H H 1518. H CD₃

H H H 1519. H CD₃

H H H 1520. H CD₃

H H H 1521. H CD₃

H H H 1522.

CD₃ CD₃ H H H 1523.

CD₃ CD₃ H H H 1524.

CD₃ CD₃ H H H 1525.

CD₃ CD₃ H H H 1526.

CD₃ CD₃ H H H 1527.

CD₃ CD₃ H H H 1528.

CD₃ CD₃ H H H 1529.

CD₃ CD₃ H H H 1530.

CD₃ CD₃ H H H 1531.

CD₃ CD₃ H H H 1532.

CD₃ CD₃ H H H 1533.

CD₃ CD₃ H H H 1534.

CD₃ CD₃ H H H 1535.

CD₃ CD₃ H H H 1536.

CD₃ CD₃ H H H 1537.

CD₃ CD₃ H H H 1538.

CD₃ CD₃ H H H 1539.

CD₃ CD₃ H H H 1540.

CD₃ CD₃ H H H 1541. CD₃

H H H H 1542. CD₃

H H H H 1543. CD₃

H H H H 1544. CD₃

H H H H 1545. CD₃

H H H H 1546. CD₃

H H H H 1547. CD₃

H H H H 1548. CD₃

H H H H 1549. CD₃

H H H H 1550. CD₃

H H H H 1551. CD₃

H H H H 1552. CD₃

H H H H 1553. CD₃

H H H H 1554. CD₃

H H H H 1555. CD₃

H H H H 1556. CD₃

H H H H 1557. CD₃

H H H H 1558. CD₃

H H H H 1559. CD₃

H H H H 1560. CD₃ CD₃

H H CD₃ 1561. CD₃ CD₃

H H CD₃ 1562. CD₃ CD₃

H H CD₃ 1563. CD₃ CD₃

H H CD₃ 1564. CD₃ CD₃

H H CD₃ 1565. CD₃ CD₃

H H CD₃ 1566. CD₃ CD₃

H H CD₃ 1567. CD₃ CD₃

H H CD₃ 1568. CD₃ CD₃

H H CD₃ 1569. CD₃ CD₃

H H CD₃ 1570. CD₃ CD₃

H H CD₃ 1571. CD₃ CD₃

H H CD₃ 1572. CD₃ CD₃

H H CD₃ 1573. CD₃ CD₃

H H CD₃ 1574. CD₃ CD₃

H H CD₃ 1575. CD₃ CD₃

H H CD₃ 1576. CD₃ CD₃

H H CD₃ 1577. CD₃ CD₃

H H CD₃ 1578. CD₃ CD₃

H H CD₃ 1579. CD₃ H

H H CD₃ 1580. CD₃ H

H H CD₃ 1581. CD₃ H

H H CD₃ 1582. CD₃ H

H H CD₃ 1583. CD₃ H

H H CD₃ 1584. CD₃ H

H H CD₃ 1585. CD₃ H

H H CD₃ 1586. CD₃ H

H H CD₃ 1587. CD₃ H

H H CD₃ 1588. CD₃ H

H H CD₃ 1589. CD₃ H

H H CD₃ 1590. CD₃ H

H H CD₃ 1591. CD₃ H

H H CD₃ 1592. CD₃ H

H H CD₃ 1593. CD₃ H

H H CD₃ 1594. CD₃ H

H H CD₃ 1595. CD₃ H

H H CD₃ 1596. CD₃ H

H H CD₃ 1597. CD₃ H

H H CD₃ 1598.

CD₃ H H H H 1599.

CD₃ H H H H 1600.

CD₃ H H H H 1601.

CD₃ H H H H 1602.

CD₃ H H H H 1603.

CD₃ H H H H 1604.

CD₃ H H H H 1605.

CD₃ H H H H 1606.

CD₃ H H H H 1607.

CD₃ H H H H 1608.

CD₃ H H H H 1609.

CD₃ H H H H 1610.

CD₃ H H H H 1611.

CD₃ H H H H 1612.

CD₃ H H H H 1613.

CD₃ H H H H 1614.

CD₃ H H H H 1615.

CD₃ H H H H 1616.

CD₃ H H H H 1617. H CD₃

H H CD₃ 1618. H CD₃

H H CD₃ 1619. H CD₃

H H CD₃ 1620. H CD₃

H H CD₃ 1621. H CD₃

H H CD₃ 1622. H CD₃

H H CD₃ 1623. H CD₃

H H CD₃ 1624. H CD₃

H H CD₃ 1625. H CD₃

H H CD₃ 1626. H CD₃

H H CD₃ 1627. H CD₃

H H CD₃ 1628. H CD₃

H H CD₃ 1629. H CD₃

H H CD₃ 1630. H CD₃

H H CD₃ 1631. H CD₃

H H CD₃ 1632. H CD₃

H H CD₃ 1633. H CD₃

H H CD₃ 1634. H CD₃

H H CD₃ 1635. H CD₃

H H CD₃ 1636. H

H H H H 1637. H

H H H H 1638. H

H H H H 1639. H

H H H H 1640. H

H H H H 1641. H

H H H H 1642. H

H H H H 1643. H

H H H H 1644. H

H H H H 1645. H

H H H H 1646. H

H H H H 1647. H

H H H H 1648. H

H H H H 1649. H

H H H H 1650. H

H H H H 1651. H

H H H H 1652. H

H H H H 1653. H

H H H H 1654. H

H H H H 1655. H

H H H H 1656. H

H H H H 1657. H

H H H H 1658. H

H H H H 1659. H

H H H H 1660. H

H H H H 1661. H

H H H H 1662. H

H H H H 1663. H

H H H H 1664. H

H H H H 1665. H

H H H H 1666. H

H H H H 1667. H

H H H H 1668. H

H H H H 1669. H

H H H H 1670. H

H H H H 1671. H

H H H H 1672. H

H H H H 1673. H

H H H H 1674. H

H H H H 1675. H

H H H H 1676. H

H H H H 1677. H

H H H H 1678. H

H H H H 1679. H

H H H H 1680. H

H H H H 1681. H

H H H H 1682. H

H H H H 1683. H

H H H H 1684. H

H H H H 1685. H

H H H H 1686. H

H H H H 1687. H

H H H H 1688. H

H H H H 1689. H

H H H H 1690. H

H H H H 1691. H

H H H H 1692. H

H H H H 1693. H

H H H H 1694. H

H H H H 1695. H

H H H H 1696. H

H H H H 1697. H

H H H H 1698. H

H H H H 1699. H

H H H H 1700. H

H H H H 1701. H

H H H H 1702. H

H H H H 1703. H

H H H H 1704. H

H H H H 1705. H

H H H H 1706. H

H H H H 1707. H

H H H H 1708. H

H H H H 1709. H

H H H H 1710. H

H H H H 1711. H

H H H H 1712. H

H H H H 1713. H

H H H H 1714. H

H H H H 1715. H

H H H H 1716. H

H H H H 1717. H

H H H H 1718. H

H H H H 1719. H

H H H H 1720. H

H H H H 1721. H

H H H H 1722. H

H H H H 1723. H

H H H H 1724. H

H H H H 1725. H

H H H H 1726. H

H H H H 1727. H

H H H H 1728. H

H H H H 1729. H

H H H H 1730. H

H H H H 1731. H

H H H H 1732. H

H H H H 1733. H

H H H H 1734. H

H H H H 1735. H

H H H H 1736. H

H H H H 1737. H

H H H H 1738. H

H H H H 1739. H

H H H H 1740. H

H H H H 1741. H

H H H H 1742. H

H H H H 1743. H

H H H H 1744. H

H H H H 1745. H

H H H H 1746. H

H H H H 1747. H

H H H H 1748. H

H H H H 1749. H

H H H H 1750. H

H H H H 1751. H

H H H H 1752. H

H H H H 1753. H

H H H H 1754. H

H H H H 1755. H

H H H H 1756. H

H H H H 1757. H

H H H H 1758. H

H H H H 1759. H

H H H H 1760. H

H H H H 1761. H

H H H H 1762. H

H H H H 1763. H

H H H H 1764. H

H H H H 1765. H

H H H H 1766. H

H H H H 1767. H

H H H H 1768. H

H H H H 1769. H

H H H H 1770. H

H H H H 1771. H

H H H H 1772. H

H H H H 1773. H

H H H H 1774. H

H H H H 1775. H

H H H H 1776. H

H H H H 1777. H

H H H H 1778. H

H H H H 1779. H

H H H H 1780. H

H H H H 1781. H

H H H H 1782. H

H H H H 1783. H

H H H H 1784. H

H H H H 1785. H

H H H H 1786. H

H H H H 1787. H

H H H H 1788. H

H H H H 1789. H

H H H H 1790. H

H H H H 1791. H

H H H H 1792. H

H H H H 1793. H

H H H H 1794. H

H H H H 1795. H

H H H H 1796. H

H H H H 1797. H

H H H H 1798. H

H H H H 1799. H

H H H H 1800. H

H H H H 1801. H

H H H H 1802. H

H H H H 1803. H

H H H H 1804. H

H H H H 1805. H H

H H H 1806. H H

H H H 1807. H H

H H H 1808. H H

H H H 1809. H H

H H H 1810. H H

H H H 1811. H H

H H H 1812. H H

H H H 1813. H H

H H H 1814. H H

H H H 1815. H H

H H H 1816. H H

H H H 1817. H H

H H H 1818. H H

H H H 1819. H H

H H H 1820. H H

H H H 1821. H H

H H H 1822. H H

H H H 1823. H H

H H H 1824. H H

H H H 1825. H H

H H H 1826. H H

H H H 1827. H H

H H H 1828. H H

H H H 1829. H H

H H H 1830. H H

H H H 1831. H H

H H H 1832. H H

H H H 1833. H H

H H H 1834. H H

H H H 1835. H H

H H H 1836. H H

H H H 1837. H H

H H H 1838. H H

H H H 1839. H H

H H H 1840. H H

H H H 1841. H H

H H H 1842. H H

H H H 1843. H H

H H H 1844. H H

H H H 1845. H H

H H H 1846. H H

H H H 1847. H H

H H H 1848. H H

H H H 1849. H H

H H H 1850. H H

H H H 1851. H H

H H H 1852. H H

H H H 1853. H H

H H H 1854. H H

H H H 1855. H H

H H H 1856. H H

H H H 1857. H H

H H H 1858. H H

H H H 1859. H H

H H H 1860. H H

H H H 1861. H H

H H H 1862. H H

H H H 1863. H H

H H H 1864. H H

H H H 1865. H H

H H H 1866. H H

H H H 1867. H H

H H H 1868. H H

H H H 1869. H H

H H H 1870. H H

H H H 1871. H H

H H H 1872. H H

H H H 1873 H H

H H H 1874. H H

H H H 1875. H H

H H H 1876. H H

H H H 1877. H H

H H H 1878. H H

H H H 1879. H H

H H H 1880. H H

H H H 1881. H H

H H H 1882. H H

H H H 1883. H H

H H H 1884. H H

H H H 1885. H H

H H H 1886. H H

H H H 1887. H H

H H H 1888. H H

H H H 1889. H H

H H H 1890. H H

H H H 1891. H H

H H H 1892. H H

H H H 1893. H H

H H H 1894. H H

H H H 1895. H H

H H H 1896. H H

H H H 1897. H H

H H H 1898. H H

H H H 1899. H H

H H H 1900. H H

H H H 1901. H H

H H H 1902. H H

H H H 1903. H H

H H H 1904. H H

H H H 1905. H H

H H H 1906. H H

H H H 1907. H H

H H H 1908. H H

H H H 1909. H H

H H H 1910. H H

H H H 1911. H H

H H H 1912. H H

H H H 1913. H H

H H H 1914. H H

H H H 1915. H H

H H H 1916. H H

H H H 1917. H H

H H H 1918. H H

H H H 1919. H H

H H H 1920. H H

H H H 1921. H H

H H H 1922. H H

H H H 1923. H H

H H H 1924. H H

H H H 1925. H H

H H H 1926. H H

H H H 1927. H H

H H H 1928. H H

H H H 1929. H H

H H H 1930. H H

H H H 1931. H H

H H H 1932. H H

H H H 1933. H H

H H H 1934. H H

H H H 1935. H H

H H H 1936. H H

H H H 1937. H H

H H H 1938. H H

H H H 1939. H H

H H H 1940. H H

H H H 1941. H H

H H H 1942. H H

H H H 1943. H H

H H H 1944. H H

H H H 1945. H H

H H H 1946. H H

H H H 1947. H H

H H H 1948. H H

H H H 1949. H H

H H H 1950. H H

H H H 1951. H H

H H H 1952. H H

H H H 1953. H H

H H H 1954. H H

H H H 1955. H H

H H H 1956. H H

H H H 1957. H H

H H H 1958. H H

H H H 1959. H H

H H H 1960. H H

H H H 1961. H H

H H H 1962. H H

H H H 1963. H H

H H H 1964. H H

H H H 1965. H H

H H H 1966. H H

H H H 1967. H H

H H H 1968. H H

H H H 1969. H H

H H H 1970. H H

H H H 1971. H H

H H H 1972. H H

H H H 1973. H H

H H H 1974. H H H

H H 1975. H H H

H H 1976. H H H

H H 1977. H H H

H H 1978. H H H

H H 1979. H H H

H H 1980. H H H

H H 1981. H H H

H H 1982. H H H

H H 1983. H H H

H H 1984. H H H

H H 1985. H H H

H H 1986. H H H

H H 1987. H H H

H H 1988. H H H

H H 1989. H H H

H H 1990. H H H

H H 1991. H H H

H H 1992. H H H

H H 1993. H H H

H H 1994. H H H

H H 1995. H H H

H H 1996. H H H

H H 1997. H H H

H H 1998. H H H

H H 1999. H H H

H H 2000. H H H

H H 2001. H H H

H H 2002. H H H

H H 2003. H H H

H H 2004. H H H

H H 2005. H H H

H H 2006. H H H

H H 2007. H H H

H H 2008. H H H

H H 2009. H H H

H H 2010. H H H

H H 2011. H H H

H H 2012. H H H

H H 2013. H H H

H H 2014. H H H

H H 2015. H H H

H H 2016. H H H

H H 2017. H H H

H H 2018. H H H

H H 2019. H H H

H H 2020. H H H

H H 2021. H H H

H H 2022. H H H

H H 2023. H H H

H H 2024. H H H

H H 2025. H H H

H H 2026. H H H

H H 2027. H H H

H H 2028. H H H

H H 2029. H H H

H H 2030. H H H

H H 2031. H H H

H H 2032. H H H

H H 2033. H H H

H H 2034. H H H

H H 2035. H H H

H H 2036. H H H

H H 2037. H H H

H H 2038. H H H

H H 2039. H H H

H H 2040. H H H

H H 2041. H H H

H H 2042. H H H

H H 2043. H H H

H H 2044. H H H

H H 2045. H H H

H H 2046. H H H

H H 2047. H H H

H H 2048. H H H

H H 2049. H H H

H H 2050. H H H

H H 2051. H H H

H H 2052. H H H

H H 2053. H H H

H H 2054. H H H

H H 2055. H H H

H H 2056. H H H

H H 2057. H H H

H H 2058. H H H

H H 2059. H H H

H H 2060. H H H

H H 2061. H H H

H H 2062. H H H

H H 2063. H H H

H H 2064. H H H

H H 2065. H H H

H H 2066. H H H

H H 2067. H H H

H H 2068. H H H

H H 2069. H H H

H H 2070. H H H

H H 2071. H H H

H H 2072. H H H

H H 2073. H H H

H H 2074. H H H

H H 2075. H H H

H H 2076. H H H

H H 2077. H H H

H H 2078. H H H

H H 2079. H H H

H H 2080. H H H

H H 2081. H H H

H H 2082. H H H

H H 2083. H H H

H H 2084. H H H

H H 2085. H H H

H H 2086. H H H

H H 2087. H H H

H H 2088. H H H

H H 2089. H H H

H H 2090. H H H

H H 2091. H H H

H H 2092. H H H

H H 2093. H H H

H H 2094. H H H

H H 2095. H H H

H H 2096. H H H

H H 2097. H H H

H H 2098. H H H

H H 2099. H H H

H H 2100. H H H

H H 2101. H H H

H H 2102. H H H

H H 2103. H H H

H H 2104. H H H

H H 2105. H H H

H H 2106. H H H

H H 2107. H H H

H H 2108. H H H

H H 2109. H H H

H H 2110. H H H

H H 2111. H H H

H H 2112. H H H

H H 2113. H H H

H H 2114. H H H

H H 2115. H H H

H H 2116. H H H

H H 2117. H H H

H H 2118. H H H

H H 2119. H H H

H H 2120. H H H

H H 2121. H H H

H H 2122. H H H

H H 2123. H H H

H H 2124. H H H

H H 2125. H H H

H H 2126. H H H

H H 2127. H H H

H H 2128. H H H

H H 2129. H H H

H H 2130. H H H

H H 2131. H H H

H H 2132. H H H

H H 2133. H H H

H H 2134. H H H

H H 2135. H H H

H H 2136. H H H

H H 2137. H H H

H H 2138. H H H

H H 2139. H H H

H H 2140. H H H

H H 2141. H H H

H H 2142. H H H

H H 2143. H H H H

H 2144. H H H H

H 2145. H H H H

H 2146. H H H H

H 2147. H H H H

H 2148. H H H H

H 2149. H H H H

H 2150. H H H H

H 2151. H H H H

H 2152. H H H H

H 2153. H H H H

H 2154. H H H H

H 2155. H H H H

H 2156. H H H H

H 2157. H H H H

H 2158. H H H H

H 2159. H H H H

H 2160. H H H H

H 2161. H H H H

H 2162. H H H H

H 2163. H H H H

H 2164. H H H H

H 2165. H H H H

H 2166. H H H H

H 2167. H H H H

H 2168. H H H H

H 2169. H H H H

H 2170. H H H H

H 2171. H H H H

H 2172. H H H H

H 2173. H H H H

H 2174. H H H H

H 2175. H H H H

H 2176. H H H H

H 2177. H H H H

H 2178. H H H H

H 2179. H H H H

H 2180. H H H H

H 2181. H H H H

H 2182. H H H H

H 2183. H H H H

H 2184. H H H H

H 2185. H H H H

H 2186. H H H H

H 2187. H H H H

H 2188. H H H H

H 2189. H H H H

H 2190. H H H H

H 2191. H H H H

H 2192. H H H H

H 2193. H H H H

H 2194. H H H H

H 2195. H H H H

H 2196. H H H H

H 2197. H H H H

H 2198. H H H H

H 2199. H H H H

H 2200. H H H H

H 2201. H H H H

H 2202. H H H H

H 2203. H H H H

H 2204. H H H H

H 2205. H H H H

H 2206. H H H H

H 2207. H H H H

H 2208. H H H H

H 2209. H H H H

H 2210. H H H H

H 2211. H H H H

H 2212. H H H H

H 2213. H H H H

H 2214. H H H H

H 2215. H H H H

H 2216. H H H H

H 2217. H H H H

H 2218. H H H H

H 2219. H H H H

H 2220. H H H H

H 2221. H H H H

H 2222. H H H H

H 2223. H H H H

H 2224. H H H H

H 2225. H H H H

H 2226. H H H H

H 2227. H H H H

H 2228. H H H H

H 2229. H H H H

H 2230. H H H H

H 2231. H H H H

H 2232. H H H H

H 2233. H H H H

H 2234. H H H H

H 2235. H H H H

H 2236. H H H H

H 2237. H H H H

H 2238. H H H H

H 2239. H H H H

H 2240. H H H H

H 2241. H H H H

H 2242. H H H H

H 2243. H H H H

H 2244. H H H H

H 2245. H H H H

H 2246. H H H H

H 2247. H H H H

H 2248. H H H H

H 2249. H H H H

H 2250. H H H H

H 2251. H H H H

H 2252. H H H H

H 2253. H H H H

H 2254. H H H H

H 2255. H H H H

H 2256. H H H H

H 2257. H H H H

H 2258. H H H H

H 2259. H H H H

H 2260. H H H H

H 2261. H H H H

H 2262. H H H H

H 2263. H H H H

H 2264. H H H H

H 2265. H H H H

H 2266. H H H H

H 2267. H H H H

H 2268. H H H H

H 2269. H H H H

H 2270. H H H H

H 2271. H H H H

H 2272. H H H H

H 2273. H H H H

H 2274. H H H H

H 2275. H H H H

H 2276. H H H H

H 2277. H H H H

H 2278. H H H H

H 2279. H H H H

H 2280. H H H H

H 2281. H H H H

H 2282. H H H H

H 2283. H H H H

H 2284. H H H H

H 2285. H H H H

H 2286. H H H H

H 2287. H H H H

H 2288. H H H H

H 2289. H H H H

H 2290. H H H H

H 2291. H H H H

H 2292. H H H H

H 2293. H H H H

H 2294. H H H H

H 2295. H H H H

H 2296. H H H H

H 2297. H H H H

H 2298. H H H H

H 2299. H H H H

H 2300. H H H H

H 2301. H H H H

H 2302. H H H H

H 2303. H H H H

H 2304. H H H H

H 2305. H H H H

H 2306. H H H H

H 2307. H H H H

H 2308. H H H H

H 2309. H H H H

H 2310. H H H H

H 2311. H H H H

H 2312. H H H H H

2313. H H H H H

2314. H H H H H

2315. H H H H H

2316. H H H H H

2317. H H H H H

2318. H H H H H

2319. H H H H H

2320. H H H H H

2321. H H H H H

2322. H H H H H

2323. H H H H H

2324. H H H H H

2325. H H H H H

2326. H H H H H

2327. H H H H H

2328. H H H H H

2329. H H H H H

2330. H H H H H

2331. H H H H H

2332. H H H H H

2333. H H H H H

2334. H H H H H

2335. H H H H H

2336. H H H H H

2337. H H H H H

2338. H H H H H

2339. H H H H H

2340. H H H H H

2341. H H H H H

2342. H H H H H

2343. H H H H H

2344. H H H H H

2345. H H H H H

2346. H H H H H

2347. H H H H H

2348. H H H H H

2349. H H H H H

2350. H H H H H

2351. H H H H H

2352. H H H H H

2353. H H H H H

2354. H H H H H

2355. H H H H H

2356. H H H H H

2357. H H H H H

2358. H H H H H

2359. H H H H H

2360. H H H H H

2361. H H H H H

2362. H H H H H

2363. H H H H H

2364. H H H H H

2365. H H H H H

2366. H H H H H

2367. H H H H H

2368. H H H H H

2369. H H H H H

2370. H H H H H

2371. H H H H H

2372. H H H H H

2373. H H H H H

2374. H H H H H

2375. H H H H H

2376. H H H H H

2377. H H H H H

2378. H H H H H

2379. H H H H H

2380. H H H H H

2381. H H H H H

2382. H H H H H

2383. H H H H H

2384. H H H H H

2385. H H H H H

2386. H H H H H

2387. H H H H H

2388. H H H H H

2389. H H H H H

2390. H H H H H

2391. H H H H H

2392. H H H H H

2393. H H H H H

2394. H H H H H

2395. H H H H H

2396. H H H H H

2397. H H H H H

2398. H H H H H

2399. H H H H H

2400. H H H H H

2401. H H H H H

2402. H H H H H

2403. H H H H H

2404. H H H H H

2405. H H H H H

2406. H H H H H

2407. H H H H H

2408. H H H H H

2409. H H H H H

2410. H H H H H

2411. H H H H H

2412. H H H H H

2413. H H H H H

2414. H H H H H

2415. H H H H H

2416. H H H H H

2417. H H H H H

2418. H H H H H

2419. H H H H H

2420. H H H H H

2421. H H H H H

2422. H H H H H

2423. H H H H H

2424. H H H H H

2425. H H H H H

2426. H H H H H

2427. H H H H H

2428. H H H H H

2429. H H H H H

2430. H H H H H

2431. H H H H H

2432. H H H H H

2433. H H H H H

2434. H H H H H

2435. H H H H H

2436. H H H H H

2437. H H H H H

2438. H H H H H

2439. H H H H H

2440. H H H H H

2441. H H H H H

2442. H H H H H

2443. H H H H H

2444. H H H H H

2445. H H H H H

2446. H H H H H

2447. H H H H H

2448. H H H H H

2449. H H H H H

2450. H H H H H

2451. H H H H H

2452. H H H H H

2453. H H H H H

2454. H H H H H

2455. H H H H H

2456. H H H H H

2457. H H H H H

2458. H H H H H

2459. H H H H H

2460. H H H H H

2461. H H H H H

2462. H H H H H

2463. H H H H H

2464. H H H H H

2465. H H H H H

2466. H H H H H

2467. H H H H H

2468. H H H H H

2469. H H H H H

2470. H H H H H

2471. H H H H H

2472. H H H H H

2473. H H H H H

2474. H H H H H

2475. H H H H H

2476. H H H H H

2477. H H H H H

2478. H H H H H

2479. H H H H H

2480. H H H H H

In some embodiments where L₁ is L_(A), the compound is Compound x selected from the group consisting of Compound 1 through Compound 2120400, where:

Compound x has the formula Ir(L_(Ai))(L_(Bj))₂, where

x=2480j+i−2480,

i is an integer from 1 to 2480,

j is an integer from 1 to 855; and

L_(Bj) is listed in the following table based on the following structure:

L_(Bj), where j is R^(B1) R^(B2) R^(B3) R^(B4)  1. H H H H  2. CH₃ H H H  3. H CH₃ H H  4. H H CH₃ H  5. H H H CH₃  6. CH₃ H CH₃ H  7. CH₃ H H CH₃  8. H CH₃ CH₃ H  9. H CH₃ H CH₃  10. H H CH₃ CH₃  11. CH₃ CH₃ CH₃ H  12. CH₃ CH₃ H CH₃  13. CH₃ H CH₃ CH₃  14. H CH₃ CH₃ CH₃  15. CH₃ CH₃ CH₃ CH₃  16. CH₂CH₃ H H H  17. CH₂CH₃ CH₃ H H  18. CH₂CH₃ H CH₃ H  19. CH₂CH₃ H H CH₃  20. CH₂CH₃ CH₃ CH₃ H  21. CH₂CH₃ CH₃ H CH₃  22. CH₂CH₃ H CH₃ CH₃  23. CH₂CH₃ CH₃ CH₃ CH₃  24. H CH₂CH₃ H H  25. CH₃ CH₂CH₃ H H  26. H CH₂CH₃ CH₃ H  27. H CH₂CH₃ H CH₃  28. CH₃ CH₂CH₃ CH₃ H  29. CH₃ CH₂CH₃ H CH₃  30. H CH₂CH₃ CH₃ CH₃  31. CH₃ CH₂CH₃ CH₃ CH₃  32. H H CH₂CH₃ H  33. CH₃ H CH₂CH₃ H  34. H CH₃ CH₂CH₃ H  35. H H CH₂CH₃ CH₃  36. CH₃ CH₃ CH₂CH₃ H  37. CH₃ H CH₂CH₃ CH₃  38. H CH₃ CH₂CH₃ CH₃  39. CH₃ CH₃ CH₂CH₃ CH₃  40. CH(CH₃)₂ H H H  41. CH(CH₃)₂ CH₃ H H  42. CH(CH₃)₂ H CH₃ H  43. CH(CH₃)₂ H H CH₃  44. CH(CH₃)₂ CH₃ CH₃ H  45. CH(CH₃)₂ CH₃ H CH₃  46. CH(CH₃)₂ H CH₃ CH₃  47. CH(CH₃)₂ CH₃ CH₃ CH₃  48. H CH(CH₃)₂ H H  49. CH₃ CH(CH₃)₂ H H  50. H CH(CH₃)₂ CH₃ H  51. H CH(CH₃)₂ H CH₃  52. CH₃ CH(CH₃)₂ CH₃ H  53. CH₃ CH(CH₃)₂ H CH₃  54. H CH(CH₃)₂ CH₃ CH₃  55. CH₃ CH(CH₃)₂ CH₃ CH₃  56. H H CH(CH₃)₂ H  57. CH₃ H CH(CH₃)₂ H  58. H CH₃ CH(CH₃)₂ H  59. H H CH(CH₃)₂ CH₃  60. CH₃ CH₃ CH(CH₃)₂ H  61. CH₃ H CH(CH₃)₂ CH₃  62. H CH₃ CH(CH₃)₂ CH₃  63. CH₃ CH₃ CH(CH₃)₂ CH₃  64. CH₂CH(CH₃)₂ H H H  65. CH₂CH(CH₃)₂ CH₃ H H  66. CH₂CH(CH₃)₂ H CH₃ H  67. CH₂CH(CH₃)₂ H H CH₃  68. CH₂CH(CH₃)₂ CH₃ CH₃ H  69. CH₂CH(CH₃)₂ CH₃ H CH₃  70. CH₂CH(CH₃)₂ H CH₃ CH₃  71. CH₂CH(CH₃)₂ CH₃ CH₃ CH₃  72. H CH₂CH(CH₃)₂ H H  73. CH₃ CH₂CH(CH₃)₂ H H  74. H CH₂CH(CH₃)₂ CH₃ H  75. H CH₂CH(CH₃)₂ H CH₃  76. CH₃ CH₂CH(CH₃)₂ CH₃ H  77. CH₃ CH₂CH(CH₃)₂ H CH₃  78. H CH₂CH(CH₃)₂ CH₃ CH₃  79. CH₃ CH₂CH(CH₃)₂ CH₃ CH₃  80. H H CH₂CH(CH₃)₂ H  81. CH₃ H CH₂CH(CH₃)₂ H  82. H CH₃ CH₂CH(CH₃)₂ H  83. H H CH₂CH(CH₃)₂ CH₃  84. CH₃ CH₃ CH₂CH(CH₃)₂ H  85. CH₃ H CH₂CH(CH₃)₂ CH₃  86. H CH₃ CH₂CH(CH₃)₂ CH₃  87. CH₃ CH₃ CH₂CH(CH₃)₂ CH₃  88. C(CH₃)₃ H H H  89. C(CH₃)₃ CH₃ H H  90. C(CH₃)₃ H CH₃ H  91. C(CH₃)₃ H H CH₃  92. C(CH₃)₃ CH₃ CH₃ H  93. C(CH₃)₃ CH₃ H CH₃  94. C(CH₃)₃ H CH₃ CH₃  95. C(CH₃)₃ CH₃ CH₃ CH₃  96. H C(CH₃)₃ H H  97. CH₃ C(CH₃)₃ H H  98. H C(CH₃)₃ CH₃ H  99. H C(CH₃)₃ H CH₃ 100. CH₃ C(CH₃)₃ CH₃ H 101. CH₃ C(CH₃)₃ H CH₃ 102. H C(CH₃)₃ CH₃ CH₃ 103. CH₃ C(CH₃)₃ CH₃ CH₃ 104. H H C(CH₃)₃ H 105. CH₃ H C(CH₃)₃ H 106. H CH₃ C(CH₃)₃ H 107. H H C(CH₃)₃ CH₃ 108. CH₃ CH₃ C(CH₃)₃ H 109. CH₃ H C(CH₃)₃ CH₃ 110. H CH₃ C(CH₃)₃ CH₃ 111. CH₃ CH₃ C(CH₃)₃ CH₃ 112. CH₂C(CH₃)₃ H H H 113. CH₂C(CH₃)₃ CH₃ H H 114. CH₂C(CH₃)₃ H CH₃ H 115. CH₂C(CH₃)₃ H H CH₃ 116. CH₂C(CH₃)₃ CH₃ CH₃ H 117. CH₂C(CH₃)₃ CH₃ H CH₃ 118. CH₂C(CH₃)₃ H CH₃ CH₃ 119. CH₂C(CH₃)₃ CH₃ CH₃ CH₃ 120. H CH₂C(CH₃)₃ H H 121. CH₃ CH₂C(CH₃)₃ H H 122. H CH₂C(CH₃)₃ CH₃ H 123. H CH₂C(CH₃)₃ H CH₃ 124. CH₃ CH₂C(CH₃)₃ CH₃ H 125. CH₃ CH₂C(CH₃)₃ H CH₃ 126. H CH₂C(CH₃)₃ CH₃ CH₃ 127. CH₃ CH₂C(CH₃)₃ CH₃ CH₃ 128. H H CH₂C(CH₃)₃ H 129. CH₃ H CH₂C(CH₃)₃ H 130. H CH₃ CH₂C(CH₃)₃ H 131. H H CH₂C(CH₃)₃ CH₃ 132. CH₃ CH₃ CH₂C(CH₃)₃ H 133. CH₃ H CH₂C(CH₃)₃ CH₃ 134. H CH₃ CH₂C(CH₃)₃ CH₃ 135. CH₃ CH₃ CH₂C(CH₃)₃ CH₃ 136. CH₂C(CH₃)₂CF₃ H H H 137. CH₂C(CH₃)₂CF₃ CH₃ H H 138. CH₂C(CH₃)₂CF₃ H CH₃ H 139. CH₂C(CH₃)₂CF₃ H H CH₃ 140. CH₂C(CH₃)₂CF₃ CH₃ CH₃ H 141. CH₂C(CH₃)₂CF₃ CH₃ H CH₃ 142. CH₂C(CH₃)₂CF₃ H CH₃ CH₃ 143. CH₂C(CH₃)₂CF₃ CH₃ CH₃ CH₃ 144. H CH₂C(CH₃)₂CF₃ H H 145. CH₃ CH₂C(CH₃)₂CF₃ H H 146. H CH₂C(CH₃)₂CF₃ CH₃ H 147. H CH₂C(CH₃)₂CF₃ H CH₃ 148. CH₃ CH₂C(CH₃)₂CF₃ CH₃ H 149. CH₃ CH₂C(CH₃)₂CF₃ H CH₃ 150. H CH₂C(CH₃)₂CF₃ CH₃ CH₃ 151. CH₃ CH₂C(CH₃)₂CF₃ CH₃ CH₃ 152. H H CH₂C(CH₃)₂CF₃ H 153. CH₃ H CH₂C(CH₃)₂CF₃ H 154. H CH₃ CH₂C(CH₃)₂CF₃ H 155. H H CH₂C(CH₃)₂CF₃ CH₃ 156. CH₃ CH₃ CH₂C(CH₃)₂CF₃ H 157. CH₃ H CH₂C(CH₃)₂CF₃ CH₃ 158. H CH₃ CH₂C(CH₃)₂CF₃ CH₃ 159. CH₃ CH₃ CH₂C(CH₃)₂CF₃ CH₃ 160. CH₂CH₂CF₃ H H H 161. CH₂CH₂CF₃ CH₃ H H 162. CH₂CH₂CF₃ H CH₃ H 163. CH₂CH₂CF₃ H H CH₃ 164. CH₂CH₂CF₃ CH₃ CH₃ H 165. CH₂CH₂CF₃ CH₃ H CH₃ 166. CH₂CH₂CF₃ H CH₃ CH₃ 167. CH₂CH₂CF₃ CH₃ CH₃ CH₃ 168. H CH₂CH₂CF₃ H H 169. CH₃ CH₂CH₂CF₃ H H 170. H CH₂CH₂CF₃ CH₃ H 171. H CH₂CH₂CF₃ H CH₃ 172. CH₃ CH₂CH₂CF₃ CH₃ H 173. CH₃ CH₂CH₂CF₃ H CH₃ 174. H CH₂CH₂CF₃ CH₃ CH₃ 175. CH₃ CH₂CH₂CF₃ CH₃ CH₃ 176. H H CH₂CH₂CF₃ H 177. CH₃ H CH₂CH₂CF₃ H 178. H CH₃ CH₂CH₂CF₃ H 179. H H CH₂CH₂CF₃ CH₃ 180. CH₃ CH₃ CH₂CH₂CF₃ H 181. CH₃ H CH₂CH₂CF₃ CH₃ 182. H CH₃ CH₂CH₂CF₃ CH₃ 183. CH₃ CH₃ CH₂CH₂CF₃ CH₃ 184.

H H H 185.

CH₃ H H 186.

H CH₃ H 187.

H H CH₃ 188.

CH₃ CH₃ H 189.

CH₃ H CH₃ 190.

H CH₃ CH₃ 191.

CH₃ CH₃ CH₃ 192. H

H H 193. CH₃

H H 194. H

CH₃ H 195. H

H CH₃ 196. CH₃

CH₃ H 197. CH₃

H CH₃ 198. H

CH₃ CH₃ 199. CH₃

CH₃ CH₃ 200. H H

H 201. CH₃ H

H 202. H CH₃

H 203. H H

CH₃ 204. CH₃ CH₃

H 205. CH₃ H

CH₃ 206. H CH₃

CH₃ 207. CH₃ CH₃

CH₃ 208.

H H H 209.

CH₃ H H 210.

H CH₃ H 211.

H H CH₃ 212.

CH₃ CH₃ H 213.

CH₃ H CH₃ 214.

H CH₃ CH₃ 215.

CH₃ CH₃ CH₃ 216. H

H H 217. CH₃

H H 218. H

CH₃ H 219. H

H CH₃ 220. CH₃

CH₃ H 221. CH₃

H CH₃ 222. H

CH₃ CH₃ 223. CH₃

CH₃ CH₃ 224. H H

H 225. CH₃ H

H 226. H CH₃

H 227. H H

CH₃ 228. CH₃ CH₃

H 229. CH₃ H

CH₃ 230. H CH₃

CH₃ 231. CH₃ CH₃

CH₃ 232.

H H H 233.

CH₃ H H 234.

H CH₃ H 235.

H H CH₃ 236.

CH₃ CH₃ H 237.

CH₃ H CH₃ 238.

H CH₃ CH₃ 239.

CH₃ CH₃ CH₃ 240. H

H H 241. CH₃

H H 242. H

CH₃ H 243. H

H CH₃ 244. CH₃

CH₃ H 245. CH₃

H CH₃ 246. H

CH₃ CH₃ 247. CH₃

CH₃ CH₃ 248. H H

H 249. CH₃ H

H 250. H CH₃

H 251. H H

CH₃ 252. CH₃ CH₃

H 253. CH₃ H

CH₃ 254. H CH₃

CH₃ 255. CH₃ CH₃

CH₃ 256.

H H H 257.

CH₃ H H 258.

H CH₃ H 259.

H H CH₃ 260.

CH₃ CH₃ H 261.

CH₃ H CH₃ 262.

H CH₃ CH₃ 263.

CH₃ CH₃ CH₃ 264. H

H H 265. CH₃

H H 266. H

CH₃ H 267. H

H CH₃ 268. CH₃

CH₃ H 269. CH₃

H CH₃ 270. H

CH₃ CH₃ 271. CH₃

CH₃ CH₃ 272. H H

H 273. CH₃ H

H 274. H CH₃

H 275. H H

CH₃ 276. CH₃ CH₃

H 277. CH₃ H

CH₃ 278. H CH₃

CH₃ 279. CH₃ CH₃

CH₃ 280.

H H H 281.

CH₃ H H 282.

H CH₃ H 283.

H H CH₃ 284.

CH₃ CH₃ H 285.

CH₃ H CH₃ 286.

H CH₃ CH₃ 287.

CH₃ CH₃ CH₃ 288. H

H H 289. CH₃

H H 290. H

CH₃ H 291. H

H CH₃ 292. CH₃

CH₃ H 293. CH₃

H CH₃ 294. H

CH₃ CH₃ 295. CH₃

CH₃ CH₃ 296. H H

H 297. CH₃ H

H 298. H CH₃

H 299. H H

CH₃ 300. CH₃ CH₃

H 301. CH₃ H

CH₃ 302. H CH₃

CH₃ 303. CH₃ CH₃

CH₃ 304.

H H H 305.

CH₃ H H 306.

H CH₃ H 307.

H H CH₃ 308.

CH₃ CH₃ H 309.

CH₃ H CH₃ 310.

H CH₃ CH₃ 311.

CH₃ CH₃ CH₃ 312. H

H H 313. CH₃

H H 314. H

CH₃ H 315. H

H CH₃ 316. CH₃

CH₃ H 317. CH₃

H CH₃ 318. H

CH₃ CH₃ 319. CH₃

CH₃ CH₃ 320. H H

H 321. CH₃ H

H 322. H CH₃

H 323. H H

CH₃ 324. CH₃ CH₃

H 325. CH₃ H

CH₃ 326. H CH₃

CH₃ 327. CH₃ CH₃

CH₃ 328. CH(CH₃)₂ H CH₂CH₃ H 329. CH(CH₃)₂ H CH(CH₃)₂ H 330. CH(CH₃)₂ H CH₂CH(CH₃)₂ H 331. CH(CH₃)₂ H C(CH₃)₃ H 332. CH(CH₃)₂ H CH₂C(CH₃)₃ H 333. CH(CH₃)₂ H CH₂CH₂CF₃ H 334. CH(CH₃)₂ H CH₂C(CH₃)₂CF₃ H 335. CH(CH₃)₂ H

H 336. CH(CH₃)₂ H

H 337. CH(CH₃)₂ H

H 338. CH(CH₃)₂ H

H 339. CH(CH₃)₂ H

H 340. CH(CH₃)₂ H

H 341. C(CH₃)₃ H CH₂CH₃ H 342. C(CH₃)₃ H CH(CH₃)₂ H 343. C(CH₃)₃ H CH₂CH(CH₃)₂ H 344. C(CH₃)₃ H C(CH₃)₃ H 345. C(CH₃)₃ H CH₂C(CH₃)₃ H 346. C(CH₃)₃ H CH₂CH₂CF₃ H 347. C(CH₃)₃ H CH₂C(CH₃)₂CF₃ H 348. C(CH₃)₃ H

H 349. C(CH₃)₃ H

H 350. C(CH₃)₃ H

H 351. C(CH₃)₃ H

H 352. C(CH₃)₃ H

H 353. C(CH₃)₃ H

H 354. CH₂C(CH₃)₃ H CH₂CH₃ H 355. CH₂C(CH₃)₃ H CH(CH₃)₂ H 356. CH₂C(CH₃)₃ H CH₂CH(CH₃)₂ H 357. CH₂C(CH₃)₃ H C(CH₃)₃ H 358. CH₂C(CH₃)₃ H CH₂C(CH₃)₃ H 359. CH₂C(CH₃)₃ H CH₂CH₂CF₃ H 360. CH₂C(CH₃)₃ H CH₂C(CH₃)₂CF₃ H 361. CH₂C(CH₃)₃ H

H 362. CH₂C(CH₃)₃ H

H 363. CH₂C(CH₃)₃ H

H 364. CH₂C(CH₃)₃ H

H 365. CH₂C(CH₃)₃ H

H 366. CH₂C(CH₃)₃ H

H 367.

H CH₂CH₃ H 368.

H CH(CH₃)₂ H 369.

H CH₂CH(CH₃)₂ H 370.

H C(CH₃)₃ H 371.

H CH₂C(CH₃)₃ H 372.

H CH₂CH₂CF₃ H 373.

H CH₂C(CH₃)₂CF₃ H 374.

H

H 375.

H

H 376.

H

H 377.

H

H 378.

H

H 379.

H

H 380.

H CH₂CH₃ H 381.

H CH(CH₃)₂ H 382.

H CH₂CH(CH₃)₂ H 383.

H C(CH₃)₃ H 384.

H CH₂C(CH₃)₃ H 385.

H CH₂CH₂CF₃ H 386.

H CH₂C(CH₃)₂CF₃ H 387.

H

H 388.

H

H 389.

H

H 390.

H

H 391.

H

H 392.

H

H 393.

H CH₂CH(CH₃)₂ H 394.

H C(CH₃)₃ H 395.

H CH₂C(CH₃)₃ H 396.

H CH₂CH₂CF₃ H 397.

H CH₂C(CH₃)₂CF₃ H 398.

H

H 399.

H

H 400.

H

H 401.

H

H 402.

H

H 403.

H

H 404.

H CH₂CH(CH₃)₂ H 405.

H C(CH₃)₃ H 406.

H CH₂C(CH₃)₃ H 407.

H CH₂CH₂CF₃ H 408.

H CH₂C(CH₃)₂CF₃ H 409.

H

H 410.

H

H 411.

H

H 412.

H

H 413.

H

H 414.

H

H 415.

H CH₂CH(CH₃)₂ H 416.

H C(CH₃)₃ H 417.

H CH₂C(CH₃)₃ H 418.

H CH₂CH₂CF₃ H 419.

H CH₂C(CH₃)₂CF₃ H 420.

H

H 421.

H

H 422.

H

H 423.

H

H 424.

H

H 425.

H

H 426. CD₃ H H H 427. H CD₃ H H 428. H H CD₃ H 429. H H H CD₃ 430. CD₃ H CD₃ H 431. CD₃ H H CD₃ 432. H CD₃ CD₃ H 433. H CD₃ H CD₃ 434. H H CD₃ CD₃ 435. CD₃ CD₃ CD₃ H 436. CD₃ CD₃ H CD₃ 437. CD₃ H CD₃ CD₃ 438. H CD₃ CD₃ CD₃ 439. CD₃ CD₃ CD₃ CD₃ 440. CD₂CH₃ H H H 441. CD₂CH₃ CD₃ H H 442. CD₂CH₃ H CD₃ H 443. CD₂CH₃ H H CD₃ 444. CD₂CH₃ CD₃ CD₃ H 445. CD₂CH₃ CD₃ H CD₃ 446. CD₂CH₃ H CD₃ CD₃ 447. CD₂CH₃ CD₃ CD₃ CD₃ 448. H CD₂CH₃ H H 449. CD₃ CD₂CH₃ H H 450. H CD₂CH₃ CD₃ H 451. H CD₂CH₃ H CD₃ 452. CD₃ CD₂CH₃ CD₃ H 453. CD₃ CD₂CH₃ H CD₃ 454. H CD₂CH₃ CD₃ CD₃ 455. CD₃ CD₂CH₃ CD₃ CD₃ 456. H H CD₂CH₃ H 457. CD₃ H CD₂CH₃ H 458. H CD₃ CD₂CH₃ H 459. H H CD₂CH₃ CD₃ 460. CD₃ CD₃ CD₂CH₃ H 461. CD₃ H CD₂CH₃ CD₃ 462. H CD₃ CD₂CH₃ CD₃ 463. CD₃ CD₃ CD₂CH₃ CD₃ 464 CD(CH₃)₂ H H H 465. CD(CH₃)₂ CD₃ H H 466. CD(CH₃)₂ H CD₃ H 467. CD(CH₃)₂ H H CD₃ 468. CD(CH₃)₂ CD₃ CD₃ H 469. CD(CH₃)₂ CD₃ H CD₃ 470. CD(CH₃)₂ H CD₃ CD₃ 471. CD(CH₃)₂ CD₃ CD₃ CD₃ 472. H CD(CH₃)₂ H H 473. CD₃ CD(CH₃)₂ H H 474. H CD(CH₃)₂ CD₃ H 475. H CD(CH₃)₂ H CD₃ 476. CD₃ CD(CH₃)₂ CD₃ H 477. CD₃ CD(CH₃)₂ H CD₃ 478. H CD(CH₃)₂ CD₃ CD₃ 479. CD₃ CD(CH₃)₂ CD₃ CD₃ 480. H H CD(CH₃)₂ H 481. CD₃ H CD(CH₃)₂ H 482. H CD₃ CD(CH₃)₂ H 483. H H CD(CH₃)₂ CD₃ 484. CD₃ CD₃ CD(CH₃)₂ H 485. CD₃ H CD(CH₃)₂ CD₃ 486. H CD₃ CD(CH₃)₂ CD₃ 487. CD₃ CD₃ CD(CH₃)₂ CD₃ 488. CD(CD₃)₂ H H H 489. CD(CD₃)₂ CD₃ H H 490. CD(CD₃)₂ H CD₃ H 491. CD(CD₃)₂ H H CD₃ 492. CD(CD₃)₂ CD₃ CD₃ H 493. CD(CD₃)₂ CD₃ H CD₃ 494. CD(CD₃)₂ H CD₃ CD₃ 495. CD(CD₃)₂ CD₃ CD₃ CD₃ 496. H CD(CD₃)₂ H H 497. CD₃ CD(CD₃)₂ H H 498. H CD(CD₃)₂ CD₃ H 499. H CD(CD₃)₂ H CD₃ 500. CD₃ CD(CD₃)₂ CD₃ H 501. CD₃ CD(CD₃)₂ H CD₃ 502. H CD(CD₃)₂ CD₃ CD₃ 503. CD₃ CD(CD₃)₂ CD₃ CD₃ 504. H H CD(CD₃)₂ H 505. CD₃ H CD(CD₃)₂ H 506. H CD₃ CD(CD₃)₂ H 507. H H CD(CD₃)₂ CD₃ 508. CD₃ CD₃ CD(CD₃)₂ H 509. CD₃ H CD(CD₃)₂ CD₃ 510. H CD₃ CD(CD₃)₂ CD₃ 511. CD₃ CD₃ CD(CD₃)₂ CD₃ 512. CD₂CH(CH₃)₂ H H H 513. CD₂CH(CH₃)₂ CD₃ H H 514. CD₂CH(CH₃)₂ H CD₃ H 515. CD₂CH(CH₃)₂ H H CD₃ 516. CD₂CH(CH₃)₂ CD₃ CD₃ H 517. CD₂CH(CH₃)₂ CD₃ H CD₃ 518. CD₂CH(CH₃)₂ H CD₃ CD₃ 519. CD₂CH(CH₃)₂ CD₃ CD₃ CD₃ 520. H CD₂CH(CH₃)₂ H H 521. CD₃ CD₂CH(CH₃)₂ H H 522. H CD₂CH(CH₃)₂ CD₃ H 523. H CD₂CH(CH₃)₂ H CD₃ 524. CD₃ CD₂CH(CH₃)₂ CD₃ H 525. CD₃ CD₂CH(CH₃)₂ H CD₃ 526. H CD₂CH(CH₃)₂ CD₃ CD₃ 527. CD₃ CD₂CH(CH₃)₂ CD₃ CD₃ 528. H H CD₂CH(CH₃)₂ H 529. CD₃ H CD₂CH(CH₃)₂ H 530. H CD₃ CD₂CH(CH₃)₂ H 531. H H CD₂CH(CH₃)₂ CD₃ 532. CD₃ CD₃ CD₂CH(CH₃)₂ H 533. CD₃ H CD₂CH(CH₃)₂ CD₃ 534. H CD₃ CD₂CH(CH₃)₂ CD₃ 535. CD₃ CD₃ CD₂CH(CH₃)₂ CD₃ 536. CD₂C(CH₃)₃ H H H 537. CD₂C(CH₃)₃ CD₃ H H 538. CD₂C(CH₃)₃ H CD₃ H 539. CD₂C(CH₃)₃ H H CD₃ 540. CD₂C(CH₃)₃ CD₃ CD₃ H 541. CD₂C(CH₃)₃ CD₃ H CD₃ 542. CD₂C(CH₃)₃ H CD₃ CD₃ 543. CD₂C(CH₃)₃ CH₃ CD₃ CD₃ 544. H CD₂C(CH₃)₃ H H 545. CD₃ CD₂C(CH₃)₃ H H 546. H CD₂C(CH₃)₃ CD₃ H 547. H CD₂C(CH₃)₃ H CD₃ 548. CD₃ CD₂C(CH₃)₃ CD₃ H 549. CD₃ CD₂C(CH₃)₃ H CD₃ 550. H CD₂C(CH₃)₃ CD₃ CD₃ 551. CD₃ CD₂C(CH₃)₃ CD₃ CD₃ 552. H H CD₂C(CH₃)₃ H 553. CD₃ H CD₂C(CH₃)₃ H 554. H CD₃ CD₂C(CH₃)₃ H 555. H H CD₂C(CH₃)₃ CD₃ 556. CD₃ CD₃ CD₂C(CH₃)₃ H 557. CD₃ H CD₂C(CH₃)₃ CD₃ 558. H CD₃ CD₂C(CH₃)₃ CD₃ 559. CD₃ CD₃ CD₂C(CH₃)₃ CD₃ 560. CD₂C(CH₃)₂CF₃ H H H 561. CD₂C(CH₃)₂CF₃ CD₃ H H 562. CD₂C(CH₃)₂CF₃ H CD₃ H 563. CD₂C(CH₃)₂CF₃ H H CD₃ 564. CD₂C(CH₃)₂CF₃ CD₃ CD₃ H 565. CD₂C(CH₃)₂CF₃ CD₃ H CD₃ 566. CD₂C(CH₃)₂CF₃ H CD₃ CD₃ 567. CD₂C(CH₃)₂CF₃ CD₃ CD₃ CD₃ 568. H CD₂C(CH₃)₂CF₃ H H 569. CD₃ CD₂C(CH₃)₂CF₃ H H 570. H CD₂C(CH₃)₂CF₃ CD₃ H 571. H CD₂C(CH₃)₂CF₃ H CD₃ 572. CD₃ CD₂C(CH₃)₂CF₃ CD₃ H 573. CD₃ CD₂C(CH₃)₂CF₃ H CD₃ 574. H CD₂C(CH₃)₂CF₃ CD₃ CD₃ 575. CD₃ CD₂C(CH₃)₂CF₃ CD₃ CD₃ 576. H H CD₂C(CH₃)₂CF₃ H 577. CD₃ H CD₂C(CH₃)₂CF₃ H 578. H CD₃ CD₂C(CH₃)₂CF₃ H 579. H H CD₂C(CH₃)₂CF₃ CD₃ 580. CD₃ CD₃ CD₂C(CH₃)₂CF₃ H 581. CD₃ H CD₂C(CH₃)₂CF₃ CD₃ 582. H CD₃ CD₂C(CH₃)₂CF₃ CD₃ 583. CD₃ CD₃ CD₂C(CH₃)₂CF₃ CD₃ 584. CD₂CH₂CF₃ H H H 585. CD₂CH₂CF₃ CD₃ H H 586. CD₂CH₂CF₃ H CD₃ H 587. CD₂CH₂CF₃ H H CD₃ 588. CD₂CH₂CF₃ CD₃ CD₃ H 589. CD₂CH₂CF₃ CD₃ H CD₃ 590. CD₂CH₂CF₃ H CD₃ CD₃ 591. CD₂CH₂CF₃ CD₃ CD₃ CD₃ 592. H CD₂CH₂CF₃ H H 593. CD₃ CD₂CH₂CF₃ H H 594. H CD₂CH₂CF₃ CD₃ H 595. H CD₂CH₂CF₃ H CD₃ 596. CD₃ CD₂CH₂CF₃ CD₃ H 597. CD₃ CD₂CH₂CF₃ H CD₃ 598. H CD₂CH₂CF₃ CD₃ CD₃ 599. CD₃ CD₂CH₂CF₃ CD₃ CD₃ 600. H H CD₂CH₂CF₃ H 601. CD₃ H CD₂CH₂CF₃ H 602. H CD₃ CD₂CH₂CF₃ H 603. H H CD₂CH₂CF₃ CD₃ 604. CD₃ CD₃ CD₂CH₂CF₃ H 605. CD₃ H CD₂CH₂CF₃ CD₃ 606. H CD₃ CD₂CH₂CF₃ CD₃ 607. CD₃ CD₃ CD₂CH₂CF₃ CD₃ 608.

H H H 609.

CD₃ H H 610.

H CD₃ H 611.

H H CD₃ 612.

CD₃ CD₃ H 613.

CD₃ H CD₃ 614.

H CD₃ CD₃ 615.

CD₃ CD₃ CD₃ 616. H

H H 617. CD₃

H H 618. H

CD₃ H 619. H

H CD₃ 620. CD₃

CD₃ H 621. CD₃

H CD₃ 622. H

CD₃ CD₃ 623. CD₃

CD₃ CD₃ 624. H H

H 625. CD₃ H

H 626. H CD₃

H 627. H H

CD₃ 628. CD₃ CD₃

H 629. CD₃ H

CD₃ 630. H CD₃

CD₃ 631. CD₃ CD₃

CD₃ 632.

H H H 633.

CD₃ H H 634.

H CD₃ H 635.

H H CD₃ 636.

CD₃ CD₃ H 637.

CD₃ H CD₃ 638.

H CD₃ CD₃ 639.

CD₃ CD₃ CD₃ 640. H

H H 641. CD₃

H H 642. H

CD₃ H 643. H

H CD₃ 644. CD₃

CD₃ H 645. CD₃

H CD₃ 646. H

CD₃ CD₃ 647. CH₃

CD₃ CD₃ 648. H H

H 649. CD₃ H

H 650. H CD₃

H 651. H H

CD₃ 652. CD₃ CD₃

H 653. CD₃ H

CD₃ 654. H CD₃

CD₃ 655. CD₃ CD₃

CD₃ 656.

H H H 657.

CD₃ H H 658.

H CD₃ H 659.

H H CD₃ 660.

CD₃ CD₃ H 661.

CD₃ H CD₃ 662.

H CD₃ CD₃ 663.

CD₃ CD₃ CD₃ 664. H

H H 665. CD₃

H H 666. H

CD₃ H 667. H

H CD₃ 668. CD₃

CD₃ H 669. CD₃

H CD₃ 670. H

CD₃ CD₃ 671. CD₃

CD₃ CD₃ 672. H H

H 673. CD₃ H

H 674. H CD₃

H 675. H H

CD₃ 676. CD₃ CD₃

H 677. CD₃ H

CD₃ 678. H CD₃

CD₃ 679. CD₃ CD₃

CD₃ 680.

H H H 681.

CD₃ H H 682.

H CD₃ H 683.

H H CD₃ 684.

CD₃ CD₃ H 685.

CD₃ H CD₃ 686.

H CD₃ CD₃ 687.

CD₃ CD₃ CD₃ 688. H

H H 689. CD₃

H H 690. H

CD₃ H 691. H

H CD₃ 692. CD₃

CD₃ H 693. CD₃

H CD₃ 694. H

CD₃ CD₃ 695. CD₃

CD₃ CD₃ 696. H H

H 697. CD₃ H

H 698. H CD₃

H 699. H H

CD₃ 700. CD₃ CD₃

H 701. CD₃ H

CD₃ 702. H CD₃

CD₃ 703. CD₃ CD₃

CD₃ 704.

H H H 705.

CD₃ H H 706.

H CD₃ H 707.

H H CD₃ 708.

CD₃ CD₃ H 709.

CD₃ H CD₃ 710.

H CD₃ CD₃ 711.

CD₃ CD₃ CD₃ 712. H

H H 713. CD₃

H H 714. H

CD₃ H 715. H

H CD₃ 716. CD₃

CD₃ H 717. CD₃

H CD₃ 718. H

CD₃ CD₃ 719. CD₃

CD₃ CD₃ 720. H H

H 721. CD₃ H

H 722. H CD₃

H 723. H H

CD₃ 724. CD₃ CD₃

H 725. CD₃ H

CD₃ 726. H CD₃

CD₃ 727. CD₃ CD₃

CD₃ 728.

H H H 729.

CD₃ H H 730.

H CD₃ H 731.

H H CD₃ 732.

CH₃ CH₃ H 733.

CD₃ H CD₃ 734.

H CD₃ CD₃ 735.

CD₃ CD₃ CD₃ 736. H

H H 737. CD₃

H H 738. H

CD₃ H 739. H

H CD₃ 740. CD₃

CD₃ H 741. CD₃

H CD₃ 742. H

CD₃ CD₃ 743. CD₃

CD₃ CD₃ 744. H H

H 745. CD₃ H

H 746. H CD₃

H 747. H H

CD₃ 748. CD₃ CD₃

H 749. CD₃ H

CD₃ 750. H CD₃

CD₃ 751. CD₃ CD₃

CD₃ 752. CD(CH₃)₂ H CD₂CH₃ H 753. CD(CH₃)₂ H CD(CH₃)₂ H 754. CD(CH₃)₂ H CD₂CH(CH₃)₂ H 755. CD(CH₃)₂ H C(CH₃)₃ H 756. CD(CH₃)₂ H CD₂C(CH₃)₃ H 757. CD(CH₃)₂ H CD₂CH₂CF₃ H 758. CD(CH₃)₂ H CD₂C(CH₃)₂CF₃ H 759. CD(CH₃)₂ H

H 760. CD(CH₃)₂ H

H 761. CD(CH₃)₂ H

H 762. CD(CH₃)₂ H

H 763. CD(CH₃)₂ H

H 764. CD(CH₃)₂ H

H 765. C(CH₃)₃ H CD₂CH₃ H 766. C(CH₃)₃ H CD(CH₃)₂ H 767. C(CH₃)₃ H CD₂CH(CH₃)₂ H 768. C(CH₃)₃ H C(CH₃)₃ H 769. C(CH₃)₃ H CD₂C(CH₃)₃ H 770. C(CH₃)₃ H CD₂CH₂CF₃ H 771. C(CH₃)₃ H CD₂C(CH₃)₂CF₃ H 772. C(CH₃)₃ H

H 773. C(CH₃)₃ H

H 774. C(CH₃)₃ H

H 775. C(CH₃)₃ H

H 776. C(CH₃)₃ H

H 777. C(CH₃)₃ H

H 778. CD₂C(CH₃)₃ H CD₂CH₃ H 779. CD₂C(CH₃)₃ H CD(CH₃)₂ H 780. CD₂C(CH₃)₃ H CD₂CH(CH₃)₂ H 781. CD₂C(CH₃)₃ H C(CH₃)₃ H 782. CD₂C(CH₃)₃ H CD₂C(CH₃)₃ H 783. CD₂C(CH₃)₃ H CD₂CH₂CF₃ H 784. CD₂C(CH₃)₃ H CD₂C(CH₃)₂CF₃ H 785. CD₂C(CH₃)₃ H

H 786. CD₂C(CH₃)₃ H

H 787. CD₂C(CH₃)₃ H

H 788. CD₂C(CH₃)₃ H

H 789. CD₂C(CH₃)₃ H

H 790. CD₂C(CH₃)₃ H

H 791.

H CD₂CH₃ H 792.

H CD(CH₃)₂ H 793.

H CD₂CH(CH₃)₂ H 794.

H C(CH₃)₃ H 795.

H CD₂C(CH₃)₃ H 796.

H CD₂CH₂CF₃ H 797.

H CD₂C(CH₃)₂CF₃ H 798.

H

H 799.

H

H 800.

H

H 801.

H

H 802.

H

H 803.

H

H 804.

H CD₂CH₃ H 805.

H CD(CH₃)₂ H 806.

H CD₂CH(CH₃)₂ H 807.

H C(CH₃)₃ H 808.

H CD₂C(CH₃)₃ H 809.

H CD₂CH₂CF₃ H 810.

H CD₂C(CH₃)₂CF₃ H 811.

H

H 812.

H

H 813.

H

H 814.

H

H 815.

H

H 816.

H

H 817.

H CD₂CH₃ H 818.

H CD(CH₃)₂ H 819.

H CD₂CH(CH₃)₂ H 820.

H C(CH₃)₃ H 821.

H CD₂C(CH₃)₃ H 822.

H CD₂CH₂CF₃ H 823.

H CD₂C(CH₃)₂CF₃ H 824.

H

H 825.

H

H 826.

H

H 827.

H

H 828.

H

H 829.

H

H 830.

H CD₂CH₃ H 831.

H CD(CH₃)₂ H 832.

H CD₂CH(CH₃)₂ H 833.

H C(CH₃)₃ H 834.

H CD₂C(CH₃)₃ H 835.

H CD₂CH₂CF₃ H 836.

H CD₂C(CH₃)₂CF₃ H 837.

H

H 838.

H

H 839.

H

H 840.

H

H 841.

H

H 842.

H

H 843.

H CD₂CH₃ H 844.

H CD(CH₃)₂ H 845.

H CD₂CH(CH₃)₂ H 846.

H C(CH₃)₃ H 847.

H CD₂C(CH₃)₃ H 848.

H CD₂CH₂CF₃ H 849.

H CD₂C(CH₃)₂CF₃ H 850.

H

H 851.

H

H 852.

H

H 853.

H

H 854.

H

H 855.

H

H

In some embodiments, the first compound can be an emissive dopant. In some embodiments, the compound can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.

In another aspect of the present disclosure, an organic light-emitting device (OLED) comprising an anode; a cathode, and an organic layer, disposed between the anode and the cathode, comprising a first compound is disclosed. The first compound is capable of functioning as a phosphorescent emitter in an organic light emitting device at room temperature, and the first compound has at least one aromatic ring and at least one substituent R, where each of the at least one substituent R is directly bonded to one of the at least one aromatic rings. Each of the at least one substituent R has the formula of

where:

G¹ is

-   -   (a) selected from the group consisting of NR¹, SiR¹R², GeR¹R²,         alkyl, cycloalkyl, and combinations thereof; and G² is a         non-aromatic polycyclic group, which can be further substituted         by one or more R³;     -   (b) a direct bond; and G² is a non-aromatic spiro polycyclic         group, which can be further substituted by one or more R³; or     -   (c) selected from the group consisting of: direct bond, NR¹,         SiR¹R², GeR¹R², alkyl, cycloalkyl, and combinations thereof; G²         is a non-aromatic polycyclic group, which can be further         substituted by one or more R³; and R is directly bonded to an         aromatic ring selected from the group consisting of phenyl,         pyridine, and triazine, which can be further fused to other         rings;

R¹, R², and R³ are independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and

each G¹ and G² is independently, optionally, partially or fully deuterated.

The OLED disclosed herein can be incorporated into one or more of a consumer product, an electronic component module, and a lighting panel. The organic layer can be an emissive layer and the compound can be an emissive dopant in some embodiments, while the compound can be a non-emissive dopant in other embodiments.

The organic layer can also include a host. In some embodiments, two or more hosts are preferred. In some embodiments, the hosts used maybe a) bipolar, b) electron transporting, c) hole transporting or d) wide band gap materials that play little role in charge transport. In some embodiments, the host can include a metal complex. The host can be a triphenylene containing benzo-fused thiophene or benzo-fused furan. Any substituent in the host can be an unfused substituent independently selected from the group consisting of C_(n)H_(2n+1), OC_(n)H_(2n+1), OAr₁, N(C_(n)H_(2n+1))₂, N(Ar₁)(Ar₂), CH═CH—C_(n)H_(2n+1), C≡C—C_(n)H_(2n+1), Ar₁, Ar₁—Ar₂, and C_(n)H_(2n)—Ar₁, or the host has no substitution. In the preceding substituents n can range from 1 to 10; and Ar₁ and Ar₂ can be independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof. The host can be an inorganic compound. For example a Zn containing inorganic material e.g. ZnS.

The host can be a compound comprising at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene. The host can include a metal complex. The host can be, but is not limited to, a specific compound selected from the group consisting of:

and combinations thereof. Additional information on possible hosts is provided below.

In yet another aspect of the present disclosure, a formulation that comprises the first compound is described. The formulation can include one or more components selected from the group consisting of a solvent, a host, a hole injection material, hole transport material, and an electron transport layer material, disclosed herein.

Combination with Other Materials

The materials described herein as useful for a particular layer in an organic light emitting device may be used in combination with a wide variety of other materials present in the device. For example, emissive dopants disclosed herein may be used in conjunction with a wide variety of hosts, transport layers, blocking layers, injection layers, electrodes and other layers that may be present. The materials described or referred to below are non-limiting examples of materials that may be useful in combination with the compounds disclosed herein, and one of skill in the art can readily consult the literature to identify other materials that may be useful in combination.

Conductivity Dopants:

A charge transport layer can be doped with conductivity dopants to substantially alter its density of charge carriers, which will in turn alter its conductivity. The conductivity is increased by generating charge carriers in the matrix material, and depending on the type of dopant, a change in the Fermi level of the semiconductor may also be achieved. Hole-transporting layer can be doped by p-type conductivity dopants and n-type conductivity dopants are used in the electron-transporting layer.

Non-limiting examples of the conductivity dopants that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP01617493, EP01968131, EP2020694, EP2684932, US20050139810, US20070160905, US20090167167, US2010288362, WO06081780, WO2009003455, WO2009008277, WO2009011327, WO2014009310, US2007252140. US2015060804 and US2012146012.

HIL/HTL:

A hole injecting/transporting material to be used in the present invention is not particularly limited, and any compound may be used as long as the compound is typically used as a hole injecting/transporting material. Examples of the material include, but are not limited to: a phthalocyanine or porphyrin derivative; an aromatic amine derivative; an indolocarbazole derivative; a polymer containing fluorohydrocarbon; a polymer with conductivity dopants; a conducting polymer, such as PEDOT/PSS; a self-assembly monomer derived from compounds such as phosphonic acid and silane derivatives; a metal oxide derivative, such as MoO_(x); a p-type semiconducting organic compound, such as 1,4,5,8,9,12-Hexaazatriphenylenehexacarbonitrile; a metal complex, and a cross-linkable compounds.

Examples of aromatic amine derivatives used in HIL or HTL include, but not limit to the following general structures:

Each of Ar¹ to Ar⁹ is selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each Ar may be unsubstituted or may be substituted by a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one aspect, Ar¹ to Ar⁹ is independently selected from the group consisting of:

wherein k is an integer from 1 to 20; X¹⁰¹ to X¹⁰⁸ is C (including CH) or N; Z¹⁰¹ is NAr¹, O, or S; Ar¹ has the same group defined above.

Examples of metal complexes used in HIL or HTL include, but are not limited to the following general formula:

wherein Met is a metal, which can have an atomic weight greater than 40; (Y¹⁰¹-Y¹⁰²) is a bidentate ligand, Y¹⁰¹ and Y¹⁰² are independently selected from C, N, O, P, and S; L¹⁰¹ is an ancillary ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.

In one aspect, (Y¹⁰¹-Y¹⁰²) is a 2-phenylpyridine derivative. In another aspect, (Y¹⁰¹-Y¹⁰²) is a carbene ligand. In another aspect, Met is selected from Ir, Pt, Os, and Zn. In a further aspect, the metal complex has a smallest oxidation potential in solution vs. Fc⁺/Fc couple less than about 0.6 V.

Non-limiting examples of the HIL and HTL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN102702075, DE102012005215, EP01624500, EP01698613, EP01806334, EP01930964, EP01972613, EP01997799, EP02011790, EP02055700, EP02055701, EP1725079, EP2085382, EP2660300, EP650955, JP07-073529, JP2005112765, JP2007091719, JP2008021687, JP2014-009196, KR20110088898, KR20130077473. TW201139402, U.S. Ser. No. 06/517,957, US20020158242, US20030162053, US20050123751, US20060182993, US20060240279, US20070145888, US20070181874, US20070278938, US20080014464, US20080091025, US20080106190, US20080124572, US20080145707, US20080220265, US20080233434, US20080303417, US2008107919, US20090115320, US20090167161, US2009066235, US2011007385, US20110163302, US2011240968, US2011278551, US2012205642, US2013241401, US20140117329, US2014183517, U.S. Pat. Nos. 5,061,569, 5,639,914, WO05075451, WO07125714, WO08023550, WO08023759, WO2009145016, WO2010061824, WO2011075644, WO2012177006, WO2013018530, WO2013039073, WO2013087142, WO2013118812, WO2013120577, WO2013157367, WO2013175747, WO2014002873, WO2014015935, WO2014015937, WO2014030872, WO2014030921, WO2014034791, WO2014104514, WO2014157018.

EBL:

An electron blocking layer (EBL) may be used to reduce the number of electrons and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies, and/or longer lifetime, as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than the emitter closest to the EBL interface. In some embodiments, the EBL material has a higher LUMO (closer to the vacuum level) and/or higher triplet energy than one or more of the hosts closest to the EBL interface. In one aspect, the compound used in EBL contains the same molecule or the same functional groups used as one of the hosts described below.

Host:

The light emitting layer of the organic EL device of the present invention preferably contains at least a metal complex as light emitting material, and may contain a host material using the metal complex as a dopant material. Examples of the host material are not particularly limited, and any metal complexes or organic compounds may be used as long as the triplet energy of the host is larger than that of the dopant. Any host material may be used with any dopant so long as the triplet criteria is satisfied.

Examples of metal complexes used as host are preferred to have the following general formula:

wherein Met is a metal; (Y¹⁰³-Y¹⁰⁴) is a bidentate ligand, Y¹⁰³ and Y¹⁰⁴ are independently selected from C, N, O, P, and S; L¹⁰¹ is an another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal; and k′+k″ is the maximum number of ligands that may be attached to the metal.

In one aspect, the metal complexes are:

wherein (O—N) is a bidentate ligand, having metal coordinated to atoms O and N.

In another aspect, Met is selected from Ir and Pt. In a further aspect, (Y¹⁰³-Y¹⁰⁴) is a carbene ligand.

Examples of other organic compounds used as host are selected from the group consisting of aromatic hydrocarbon cyclic compounds such as benzene, biphenyl, triphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, and azulene; the group consisting of aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridylindole, pyrrolodipyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, phenoxazine, benzofuropyridine, furodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, and selenophenodipyridine; and the group consisting of 2 to 10 cyclic structural units which are groups of the same type or different types selected from the aromatic hydrocarbon cyclic group and the aromatic heterocyclic group and are bonded to each other directly or via at least one of oxygen atom, nitrogen atom, sulfur atom, silicon atom, phosphorus atom, boron atom, chain structural unit and the aliphatic cyclic group. Each option within each group may be unsubstituted or may be substituted by a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof.

In one aspect, the host compound contains at least one of the following groups in the molecule:

wherein each of R¹⁰¹ to R¹⁰⁷ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, and when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. k is an integer from 0 to 20 or 1 to 20; k′″ is an integer from 0 to 20. X¹⁰¹ to X¹⁰⁸ is selected from C (including CH) or N. Z¹⁰¹ and Z¹⁰² is selected from NR¹⁰¹, O, or S.

Non-limiting examples of the host materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: EP2034538, EP2034538A, EP2757608, JP2007254297, KR20100079458, KR20120088644, KR20120129733, KR20130115564, TW201329200, US20030175553, US20050238919, US20060280965, US20090017330, US20090030202, US20090167162, US20090302743, US20090309488, US20100012931, US20100084966, US20100187984, US2010187984, US2012075273, US2012126221, US2013009543, US2013105787, US2013175519, US2014001446, US20140183503, US20140225088, US2014034914, U.S. Pat. No. 7,154,114, WO2001039234, WO2004093207, WO2005014551, WO2005089025, WO2006072002, WO2006114966, WO2007063754, WO2008056746, WO2009003898, WO2009021126, WO2009063833, WO2009066778, WO2009066779, WO2009086028, WO2010056066, WO2010107244, WO2011081423, WO2011081431. WO2011086863, WO2012128298, WO2012133644, WO2012133649, WO2013024872, WO2013035275, WO2013081315, WO2013191404, WO2014142472,

Additional Emitters:

One or more additional emitter dopants may be used in conjunction with the compound of the present disclosure. Examples of the additional emitter dopants are not particularly limited, and any compounds may be used as long as the compounds are typically used as emitter materials. Examples of suitable emitter materials include, but are not limited to, compounds which can produce emissions via phosphorescence, fluorescence, thermally activated delayed fluorescence, i.e., TADF (also referred to as E-type delayed fluorescence), triplet-triplet annihilation, or combinations of these processes.

Non-limiting examples of the emitter materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103694277, CN1696137, EB01238981, EP01239526, EP01961743, EP1239526, EP1244155, EP1642951, EP1647554 EP1841834, EP1841834B, EP2062907, EP2730583, JP2012074444, JP2013110263, JP4478555, KR1020090133652, KR20120032054, KR20130043460, TW201332980. U.S. Ser. No. 06/699,599, U.S. Ser. No. 06/916,554, US20010019782, US20020034656, US20030068526, US20030072964, US20030138657, US20050123788, US20050244673, US2005123791, US2005260449, US20060008670, US20060065890, US20060127696, US20060134459, US20060134462, US20060202194, US20060251923, US20070034863, US20070087321, US20070103060, US20070111026, US20070190359, US20070231600, US2007034863, US2007104979, US2007104980, US2007138437, US2007224450, US2007278936, US20080020237, US20080233410. US20080261076, US20080297033, US200805851, US2008161567, US2008210930, US20090039776, US20090108737, US20090115322, US20090179555, US2009085476, US2009104472, US20100090591, US20100148663, US20100244004, US20100295032, US2010102716, US2010105902, US2010244004, US2010270916, US20110057559, US20110108822, US20110204333, US2011215710, US2011227049, US2011285275, US2012292601, US20130146848, US2013033172, US2013165653, US2013181190, US2013334521, US20140246656, US2014103305, U.S. Pat. Nos. 6,303,238, 6,413,656, 6,653,654, 6,670,645, 6,687,266, 6,835,469, 6,921,915, 7,279,704, 7,332,232, 7,378,162, 7,534,505, 7,675,228, 7,728,137, 7,740,957, 7,759,489, 7,951,947, 8,067,099, 8,592,586, 8,871,361, WO06081973, WO06121811, WO07018067, WO07108362, WO07115970, WO07115981, WO08035571, WO2002015645, WO2003040257, WO2005019373, WO2006056418, WO2008054584, WO2008078800, WO2008096609, WO2008101842, WO2009000673, WO2009050281, WO2009100991, WO2010028151, WO2010054731, WO2010086089, WO2010118029, WO2011044988, WO2011051404, WO2011107491, WO2012020327, WO2012163471, WO2013094620, WO2013107487, WO2013174471, WO2014007565, WO2014008982, WO2014023377, WO2014024131, WO2014031977, WO2014038456, WO2014112450.

HBL:

A hole blocking layer (HBL) may be used to reduce the number of holes and/or excitons that leave the emissive layer. The presence of such a blocking layer in a device may result in substantially higher efficiencies and/or longer lifetime as compared to a similar device lacking a blocking layer. Also, a blocking layer may be used to confine emission to a desired region of an OLED. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and or higher triplet energy than the emitter closest to the HBL interface. In some embodiments, the HBL material has a lower HOMO (further from the vacuum level) and or higher triplet energy than one or more of the hosts closest to the HBL interface.

In one aspect, compound used in HBL contains the same molecule or the same functional groups used as host described above.

In another aspect, compound used in HBL contains at least one of the following groups in the molecule:

wherein k is an integer from 1 to 20; L¹⁰¹ is an another ligand, k′ is an integer from 1 to 3. ETL:

Electron transport layer (ETL) may include a material capable of transporting electrons. Electron transport layer may be intrinsic (undoped), or doped. Doping may be used to enhance conductivity. Examples of the ETL material are not particularly limited, and any metal complexes or organic compounds may be used as long as they are typically used to transport electrons.

In one aspect, compound used in ETL contains at least one of the following groups in the molecule:

wherein R¹⁰¹ is selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof, when it is aryl or heteroaryl, it has the similar definition as Ar's mentioned above. Ar¹ to Ar³ has the similar definition as Ar's mentioned above. k is an integer from 1 to 20. X¹⁰¹ to X¹⁰⁸ is selected from C (including CH) or N.

In another aspect, the metal complexes used in ETL contains, but not limit to the following general formula:

wherein (O—N) or (N—N) is a bidentate ligand, having metal coordinated to atoms O, N or N, N; L¹⁰¹ is another ligand; k′ is an integer value from 1 to the maximum number of ligands that may be attached to the metal.

Non-limiting examples of the ETL materials that may be used in an OLED in combination with materials disclosed herein are exemplified below together with references that disclose those materials: CN103508940, EP01602648, EP01734038, EP01956007, JP2004-022334, JP2005149918, JP2005-268199, KR0117693, KR20130108183, US20040036077, US20070104977, US2007018155, US20090101870, US20090115316, US20090140637, US20090179554, US2009218940, US2010108990, US2011156017, US2011210320, US2012193612, US2012214993, US2014014925, US2014014927, US20140284580, U.S. Pat. Nos. 6,656,612, 8,415,031, WO2003060956, WO2007111263, WO2009148269, WO2010067894, WO2010072300, WO2011074770, WO2011105373, WO2013079217, WO2013145667, WO2013180376, WO2014104499, WO2014104535,

Charge Generation Layer (CGL)

In tandem or stacked OLEDs, the CGL plays an essential role in the performance, which is composed of an n-doped layer and a p-doped layer for injection of electrons and holes, respectively. Electrons and holes are supplied from the CGL and electrodes. The consumed electrons and holes in the CGL are refilled by the electrons and holes injected from the cathode and anode, respectively, then, the bipolar currents reach a steady state gradually. Typical CGL materials include n and p conductivity dopants used in the transport layers.

In any above-mentioned compounds used in each layer of the OLED device, the hydrogen atoms can be partially or fully deuterated. Thus, any specifically listed substituent, such as, without limitation, methyl, phenyl, pyridyl, etc. may be undeuterated, partially deuterated, and fully deuterated versions thereof. Similarly, classes of substituents such as, without limitation, alkyl, aryl, cycloalkyl, heteroaryl, etc. also may be undeuterated, partially deuterated, and fully deuterated versions thereof.

EXPERIMENTAL Synthesis Examples Synthesis Example 1 Synthesis of 8-(4-(bicyclo[2.2.1]heptan-2-yl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine

8-(4-chloropyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (4.75 g, 16.12 mmol) and [1,3-Bis(2,6-Diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride (PEPPSI-IPr) (1.094 g, 1.612 mmol) were charged into a reaction flask with 50 mL of tetrahydrofuran (THF). This mixture was degassed with nitrogen then was stirred at room temperature (˜22° C.). Then, bicyclo[2.2.1]heptan-2-ylzinc(II) bromide (97 ml, 48.3 mmol) was added to the reaction mixture via syringe. Stirring was continued at room temperature for 18 hours. The reaction mixture was quenched with aqueous ammonium chloride solution, then extracted with ethyl acetate. The extracts were dried over magnesium sulfate then filtered and concentrated to a reduced volume under vacuum. A solid was filtered from the resulting concentrate. The filtrate was passed through a silica gel column eluting with 2.5-5% THF/dichloromethane (DCM). The cleanest fractions were combined and concentrated under vacuum yielding 8-(4-(bicyclo[2.2.1]heptan-2-yl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (4 g, 11.28 mmol, 70.0% yield) as a viscous light yellow oil.

Synthesis of 8-(4-(bicyclo[2.2.1]heptan-2-yl-2-d)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine

8-(4-(bicyclo[2.2.1]heptan-2-yl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (4 g, 11.28 mmol) was dissolved in 40 mL of THF. Dimethyl sulfoxide-d₆ (37.9 g, 451 mmol) was syringed into the reaction mixture, followed by the addition of sodium tert-butoxide (0.542 g, 5.64 mmol). The resulting mixture was stirred and heated for 20 hours in a bath set at 65° C. The reaction mixture was quenched with 80 mL of D₂O. The mixture was extracted two times with 400 mL ethyl acetate. The extracts were combined, washed with an aqueous LiCl solution, then dried over magnesium sulfate. The extracts were then filtered and concentrated under vacuum. The residue was passed through 3×120 g silica gel columns using 2.5-3.5% THF/DCM. The clean product fractions yielded 8-(4-(bicyclo[2.2.1]heptan-2-yl-2-d)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine (2.7 g, 7.53 mmol, 66.7% yield).

Synthesis of Compound 1064460 [Ir(L_(A540))(L_(B430))₂]

8-(4-(bicyclo[2.2.1]heptan-2-yl-2-d)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine (2.6 g, 7.25 mmol) and the iridium salt shown in the synthetic scheme above (3.28 g, 4.19 mmol) were charged into a reaction flask with ethanol (32 mL) and methanol (32 mL). The reaction mixture was degassed with nitrogen then was heated for 3 days in an oil bath set at 70° C. The oil bath temperature was then raised to 80° C. and the reaction mixture was stirred for two additional days. After this time, the reaction flask was cooled to room temperature (˜20° C.). A yellow solid was isolated via filtration and was dried under vacuum with no heat. This solid was dissolved in toluene and was pre-absorbed on silica gel. This material was purified using silica gel chromatography through 6×125 g silica gel cartridges eluting with 0.7-0.8% ethyl acetate/toluene to yield a yellow solid that was triturated twice with hot toluene. Compound 1064460 was then isolated as a yellow solid via filtration (0.60 g, 0.646 mmol, 15.4% yield) LC/MS confirmed the mass of the desired product.

Synthesis Example 2 Synthesis of 8-(5-(bicyclo[2.2.1 l]heptan-2-yl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine

8-(5-bromopyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (7 g, 20.64 mmol) and PEPPSI-IPr (1.051 g, 1.548 mmol) were charged into the reaction flask with 150 mL of THF. Bicyclo[2.2.1]heptan-2-ylzinc(II) bromide (70.2 ml, 35.1 mmol) was then syringed into the reaction flask and the mixture was degassed with nitrogen. This mixture was stirred at room temperature (˜22° C.) for 16 hours. Gas chromatography/mass spectroscopy analysis showed the reaction to be complete. The reaction mixture was quenched with aqueous ammonium chloride, then the majority of the THF was removed under reduced pressure. Ethyl acetate was added to the aqueous mixture and this mixture was heated for several hours in a 70° C. bath. The organic layer was then separated and the aqueous layer was again extracted with ethyl acetate. The extracts were combined, washed with aqueous LiCl, then dried over magnesium sulfate. The extracts were then filtered and concentrated under vacuum. The crude residue was passed through 2×330 g silica gel columns using 3-6% THF/toluene. Clean product fractions were combined and concentrated under vacuum yielding 8-(5-(bicyclo[2.2.1]heptan-2-yl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (6 g, 16.93 mmol, 82% yield) as a foamy solid.

Synthesis of 8-(5-(bicyclo[2.2.1]heptan-2-yl-2-d)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine

8-(5-(bicyclo[2.2.1]heptan-2-yl)pyridin-2-yl)-2-methylbenzofuro[2,3-b]pyridine (7.34 g, 20.71 mmol) was charged into a reaction flask with 60 mL of THF and dimethyl sulfoxide-d6 (35 ml, 500 mmol). Sodium tert-butoxide (0.596 g, 6.21 mmol) was then added all at once to the reaction mixture. This mixture was stirred and heated for 16 hours in an oil bath set at 65° C. The reaction mixture was cooled to room temperature (˜22° C.) then was quenched with 80 mL of D₂O. The mixture was extracted two times with 400 mL ethyl acetate. The extracts were combined, washed with aqueous LiCl, then dried over magnesium sulfate. The extracts were then filtered and concentrated under vacuum. The residue was passed through 3×330 g silica gel columns using 2.5-3.5% THF/toluene. Clean product fractions yielded 8-(5-(bicyclo[2.2.1]heptan-2-yl-2-d)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine (3.3 g, 9.21 mmol, 44.5% yield).

Synthesis of Compound 1064122 [Ir(L_(A202))(L_(B430))₂]

8-(5-(bicyclo[2.2.1]heptan-2-yl-2-d)pyridin-2-yl)-2-(methyl-d3)benzofuro[2,3-b]pyridine (3.3 g, 9.21 mmol) and the iridium salt shown in the scheme above (4.2 g, 5.37 mmol) were charged into the reaction flask with 40 mL ethanol and 40 mL methanol. This mixture was degassed with nitrogen then heated for five days in an oil bath set at 75° C. The reaction mixture was cooled to room temperature (˜22° C.). A yellow solid was filtered from solution, which was then dried under vacuum. The yellow solid was dissolved in 400 mL of DCM and then passed through an activated plug of basic alumina. The DCM filtrate was evaporated under reduced vacuum. The crude residue was passed through 7×120 g silica gel columns eluting the columns with 5% ethyl acetate/toluene. The major product eluted 1^(st) from the columns was isolated as a yellow solid. This material was triturated twice with toluene/heptane then isolated via filtration. The desired iridium complex was isolated as a yellow solid (0.8 g, 0.86 mmoL, 16.06% yield). Liquid chromatography/mass spectroscopy (LC/MS) analysis confirmed the mass of the desired product.

Device Examples

All example devices were fabricated by high vacuum (<10-7 Torr) thermal evaporation. The anode electrode was 750 Å of indium tin oxide (ITO). The cathode consisted of 10 Å of Liq (8-hydroxyquinoline lithium) followed by 1,000 Å of Al. All devices were encapsulated with a glass lid sealed with an epoxy resin in a nitrogen glove box (<1 ppm of H₂O and O₂) immediately after fabrication, and a moisture getter was incorporated inside the package. The stack of the device examples consisted of sequentially, from the ITO surface, 100 Å of HATCN as the hole injection layer (HIL); 450 Å of HTM as a hole transporting layer (HTL); 50 Å of EBM as electron blocking layer, 400 Å of EML containing two component host (H1:H2 3:2 ratio) and emitter 12% (GD1 as Inventive Example 1 vs GD2 as comparison example CE 1), and 350 Å of Liq (8-hydroxyquinoline lithium) doped with 40% of ETM as the ETL. The chemical structures of the device materials are shown below.

Table 1 shows the device layer thicknesses and materials.

TABLE 1 Device structure for evaluation of green emitters Layer Material Thickness [Å] Anode ITO 750 HIL HATCN 100 HTL HTM 450 EBL EBM 50 G EML H1:H2 (3:2): Emitter 12% 350 ETL Liq: ETM 40% 350 EIL Liq 10 Cathode Al 1000

Emitter Example 1 (GD1) and Comparative Example CE1 (GD2) were used to demonstrate the superiority efficiency of the device with inventive vs. comparative compounds. The device External quantum efficiency (EQE) and luminance efficacy (LE) measured 10 mA/cm² are shown in the Table 2.

TABLE 2 External quantum efficiency of devices with inventive and comparative examples Example Emitter LE at 10 mA/cm² [cd/A] EQE at 10 mA/cm² [%] CE1 GD2 93.3 24.4 Example 1 GD1 98.1 25.7

The observed device LE and EQE of inventive emitter is significantly higher vs. comparative emitter.

It is understood that the various embodiments described herein are by way of example only, and are not intended to limit the scope of the invention. For example, many of the materials and structures described herein may be substituted with other materials and structures without deviating from the spirit of the invention. The present invention as claimed may therefore include variations from the particular examples and preferred embodiments described herein, as will be apparent to one of skill in the art. It is understood that various theories as to why the invention works are not intended to be limiting. 

We claim:
 1. A composition comprising a first compound having the formula of M(L¹)_(x)(L²)_(y)(L³)_(z); wherein L¹, L² and L³ can be the same or different; wherein x is 1, 2, or 3; wherein v is 0, 1, or 2; wherein z is 0, 1, or 2; wherein x+v+z is the oxidation state of a metal M; wherein the metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu; wherein ligand L¹ has at least one substituent R bonded to an aromatic ring by a single bond; wherein each of the at least one substituent R has the formula of

and is a monovalent substituent; wherein G¹ is selected from the group consisting of: a single bond, NR¹, SiR¹R², GeR¹R², alkyl, cycloalkyl, and combinations thereof; and G² is a non-aromatic spiro polycyclic group, which can be further substituted by one or more R³; wherein L¹ is a first ligand selected from the group consisting of:

wherein L² and L³ are each independently one ligand selected from the group for the first ligand or

wherein each X¹ to X¹⁷ is independently selected from the group consisting of carbon and nitrogen; wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO₂, CR′R″, SiR′R″, and GeR′R″; wherein each R′ and R″ is independently, optionally fused or joined to form a ring; wherein each R_(a), R_(b), R_(c), and R_(d) independently represents from mono substitution to the maximum possible number of substitutions, or no substitution; wherein each R′, R″, R_(a), R_(b), R_(c), R_(d), R¹, R², and R³ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; provided that for L¹, at least one R_(a), R_(b), R_(c), or R_(d) is substituent R or comprises an aromatic ring to which substituent R is single bonded; wherein each G¹ and G² is independently, optionally, partially or fully deuterated; and wherein, excluding the at least one substituent R, any two adjacent substituents of R_(a), R_(b), R_(c), and R_(d) are optionally fused or joined to form a ring or form a multidentate ligand.
 2. The composition of claim 1, wherein G² is polycyclic alkyl.
 3. The composition of claim 1, wherein G² contains at least one heteroatom.
 4. The composition of claim 1, wherein the first compound is capable of emitting light from a triplet excited state to a ground singlet state at room temperature.
 5. The composition of claim 1, wherein the first compound has the formula of Ir(L¹)₂(L²).
 6. The composition of claim 5, wherein L¹ has the formula selected from the group consisting of:

and wherein L² has the formula:


7. The composition of claim 5, wherein L¹ and L² are different and each independently selected from the group consisting of:


8. The composition of claim 5, wherein L¹ and L² are each independently selected from the group consisting of:


9. The composition of claim 1, wherein G² is a moiety selected from the group consisting of:

which can be further substituted by R³.
 10. The composition of claim 1, wherein each of the at least one substituent R is independently selected from the group consisting of:


11. An organic light-emitting device (OLED) comprising: an anode; a cathode; and an organic layer, disposed between the anode and the cathode, comprising a first compound having the formula of M(L¹)_(x)(L²)_(y)(L³)_(z); wherein L¹, L² and L³ can be the same or different; wherein x is 1, 2, or 3; wherein v is 0, 1, or 2; wherein z is 0, 1, or 2; wherein x+v+z is the oxidation state of a metal M; wherein the metal M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu; wherein ligand L¹ has at least one substituent R bonded to an aromatic ring by a single bond; wherein each of the at least one substituent R has the formula of

and is a monovalent substituent; wherein G¹ is selected from the group consisting of: a single bond, NR¹, SiR¹R², GeR¹R², alkyl, cycloalkyl, and combinations thereof; and G² is a non-aromatic spiro polycyclic group, which can be further substituted by one or more R³; wherein L¹ is a first ligand selected from the group consisting of:

wherein L² and L³ are each independently one ligand selected from the group for the first ligand or

wherein each X¹ to X¹⁷ is independently selected from the group consisting of carbon and nitrogen; wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C═O, S═O, SO₂, CR′R″, SiR′R″, and GeR′R″; wherein each R′ and R″ is independently, optionally fused or joined to form a ring; wherein each R_(a), R_(b), R_(c), and R_(d) independently represents from mono substitution to the maximum possible number of substitutions, or no substitution; wherein each R′, R″, R_(a), R_(b), R_(c), R_(d), R¹, R², and R³ is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; provided that for L¹, at least one R_(a), R_(b), R_(c), or R_(d) is substituent R or comprises an aromatic ring to which substituent R is single bonded; wherein each G¹ and G² is independently, optionally, partially or fully deuterated; and wherein, excluding the at least one substituent R, any two adjacent substituents of R_(a), R_(b), R_(c), and R_(d) are optionally fused or joined to form a ring or form a multidentate ligand.
 12. The OLED of claim 11, wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.
 13. The OLED of claim 11, wherein the organic layer is an emissive layer and the first compound is an emissive dopant.
 14. The OLED of claim 11, wherein the organic layer further comprises a host, wherein host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, aza-triphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
 15. The OLED of claim 11, wherein the organic layer further comprises a host, wherein the host is selected from the group consisting of:

and combinations thereof.
 16. A formulation comprising the composition in claim
 1. 17. The composition of claim 1, wherein L¹ has the following structure:

selected from the group consisting of L₁ ¹ to L₂₄₈ ¹ as listed below: L¹ _(i), i R_(A1) R_(A2) R_(A3)
 1.

H H
 2.

H H
 3.

H H
 4.

H H
 5.

H H
 6.

H H
 7.

H H
 8.

H H
 9.

H H
 10.

H H
 11.

H H
 12.

H H
 13.

H H
 14.

H H
 15.

H H
 16.

H H
 17.

H CD₃
 18.

H CD₃
 19.

H CD₃
 20.

H CD₃
 21.

H CD₃
 22.

H CD₃
 23.

H CD₃
 24.

H CD₃
 25.

H CD₃
 26.

H CD₃
 27.

H CD₃
 28.

H CD₃
 29.

H CD₃
 30.

H CD₃
 31.

H CD₃
 32.

H CD₃
 33.

CD₃ CD₃
 34.

CD₃ CD₃
 35.

CD₃ CD₃
 36.

CD₃ CD₃
 37.

CD₃ CD₃
 38.

CD₃ CD₃
 39.

CD₃ CD₃
 40.

CD₃ CD₃
 41.

CD₃ CD₃
 42.

CD₃ CD₃
 43.

CD₃ CD₃
 44.

CD₃ CD₃
 45.

CD₃ CD₃
 46.

CD₃ CD₃
 47.

CD₃ CD₃
 48.

CD₃ CD₃
 49. H

CD₃
 50. H

CD₃
 51. H

CD₃
 52. H

CD₃
 53. H

CD₃
 54. H

CD₃
 55. H

CD₃
 56. H

CD₃
 57. H

CD₃
 58. H

CD₃
 59. H

CD₃
 60. H

CD₃
 61. H

CD₃
 62. H

CD₃
 63. H

CD₃
 64. H

CD₃
 65. CD₃

CD₃
 66. CD₃

CD₃
 67. CD₃

CD₃
 68. CD₃

CD₃
 69. CD₃

CD₃
 70. CD₃

CD₃
 71. CD₃

CD₃
 72. CD₃

CD₃
 73. CD₃

CD₃
 74. CD₃

CD₃
 75. CD₃

CD₃
 76. CD₃

CD₃
 77. CD₃

CD₃
 78. CD₃

CD₃
 79. CD₃

CD₃
 80. CD₃

CD₃
 81. CD₃

CD₃
 82. CD₃

CD₃
 83. CD₃

CD₃
 84. CD₃

CD₃
 85. CD₃

CD₃
 86. CD₃

CD₃
 87. CD₃

CD₃
 88. CD₃

CD₃
 89. CD₃

CD₃
 90. CD₃

CD₃
 91. CD₃

CD₃
 92. CD₃

CD₃
 93. CD₃

CD₃
 94. CD₃

CD₃
 95. CD₃

CD₃
 96. CD₃

CD₃
 97. CD₃ CD₃


98. CD₃ CD₃


99. CD₃ CD₃


100. CD₃ CD₃


101. CD₃ CD₃


102. CD₃ CD₃


103. CD₃ CD₃


104. CD₃ CD₃


105. CD₃ CD₃


106. CD₃ CD₃


107. CD₃ CD₃


108. CD₃ CD₃


109. CD₃ CD₃


110. CD₃ CD₃


111. CD₃ CD₃


112. CD₃ CD₃


113. CD₃ H


114. CD₃ H


115. CD₃ H


116. CD₃ H


117. CD₃ H


118. CD₃ H


119. CD₃ H


120. CD₃ H


121. CD₃ H


122. CD₃ H


123. CD₃ H


124. CD₃ H


125. CD₃ H


126. CD₃ H


127. CD₃ H


128. CD₃ H


129. H CD₃


130. H CD₃


131. H CD₃


132. H CD₃


133. H CD₃


134. H CD₃


135. H CD₃


136. H CD₃


137. H CD₃


138. H CD₃


139. H CD₃


140. H CD₃


141. H CD₃


142. H CD₃


143. H CD₃


144. H CD₃


145.

CD₃ CD₃
 146.

CD₃ CD₃
 147.

CD₃ CD₃
 148.

CD₃ CD₃
 149. CD₃

H
 150. CD₃

H
 151. CD₃

H
 152. CD₃

H
 153. CD₃ CD₃


154. CD₃ CD₃


155. CD₃ CD₃


156. CD₃ CD₃


157. CD₃ H


158. CD₃ H


159. CD₃ H


160. CD₃ H


161.

CD₃ H
 162.

CD₃ H
 163.

CD₃ H
 164.

CD₃ H
 165. H CD₃


166. H CD₃


167. H CD₃


168. H CD₃


169. H

H
 170. H

H
 171. H

H
 172. H

H
 173. H

H
 174. H

H
 175. H

H
 176. H

H
 177. H

H
 178. H

H
 179. H

H
 180. H

H
 181. H

H
 182. H

H
 183. H

H
 184. H

H
 185. H H


186. H H


187. H H


188. H H


189. H H


190. H H


191. H H


192. H H


193. H H


194. H H


195. H H


196. H H


197. H H


198. H H


199. H H


200. H H


201. H H H
 202. H H H
 203. H H H
 204. H H H
 205. H H H
 206. H H H
 207. H H H
 208. H H H
 209. H H H
 210. H H H
 211. H H H
 212. H H H
 213. H H H
 214. H H H
 215. H H H
 216. H H H
 217. H H H
 218. H H H
 219. H H H
 220. H H H
 221. H H H
 222. H H H
 223. H H H
 224. H H H
 225. H H H
 226. H H H
 227. H H H
 228. H H H
 229. H H H
 230. H H H
 231. H H H
 232. H H H
 233. H H H
 234. H H H
 235. H H H
 236. H H H
 237. H H H
 238. H H H
 239. H H H
 240. H H H
 241. H H H
 242. H H H
 243. H H H
 244. H H H
 245. H H H
 246. H H H
 247. H H H
 248. H H H L¹ _(i,) i R_(A4) R_(A5) R_(A6)
 1. H H H
 2. H H H
 3. H H H
 4. H H H
 5. H H H
 6. H H H
 7. H H H
 8. H H H
 9. H H H
 10. H H H
 11. H H H
 12. H H H
 13. H H H
 14. H H H
 15. H H H
 16. H H H
 17. H H H
 18. H H H
 19. H H H
 20. H H H
 21. H H H
 22. H H H
 23. H H H
 24. H H H
 25. H H H
 26. H H H
 27. H H H
 28. H H H
 29. H H H
 30. H H H
 31. H H H
 32. H H H
 33. H H CD₃
 34. H H CD₃
 35. H H CD₃
 36. H H CD₃
 37. H H CD₃
 38. H H CD₃
 39. H H CD₃
 40. H H CD₃
 41. H H CD₃
 42. H H CD₃
 43. H H CD₃
 44. H H CD₃
 45. H H CD₃
 46. H H CD₃
 47. H H CD₃
 48. H H CD₃
 49. H H H
 50. H H H
 51. H H H
 52. H H H
 53. H H H
 54. H H H
 55. H H H
 56. H H H
 57. H H H
 58. H H H
 59. H H H
 60. H H H
 61. H H H
 62. H H H
 63. H H H
 64. H H H
 65. H H CD₃
 66. H H CD₃
 67. H H CD₃
 68. H H CD₃
 69. H H CD₃
 70. H H CD₃
 71. H H CD₃
 72. H H CD₃
 73. H H CD₃
 74. H H CD₃
 75. H H CD₃
 76. H H CD₃
 77. H H CD₃
 78. H H CD₃
 79. H H CD₃
 80. H H CD₃
 81. H H H
 82. H H H
 83. H H H
 84. H H H
 85. H H H
 86. H H H
 87. H H H
 88. H H H
 89. H H H
 90. H H H
 91. H H H
 92. H H H
 93. H H H
 94. H H H
 95. H H H
 96. H H H
 97. H H H
 98. H H H
 99. H H H
 100. H H H
 101. H H H
 102. H H H
 103. H H H
 104. H H H
 105. H H H
 106. H H H
 107. H H H
 108. H H H
 109. H H H
 110. H H H
 111. H H H
 112. H H H
 113. H H H
 114. H H H
 115. H H H
 116. H H H
 117. H H H
 118. H H H
 119. H H H
 120. H H H
 121. H H H
 122. H H H
 123. H H H
 124. H H H
 125. H H H
 126. H H H
 127. H H H
 128. H H H
 129. H H H
 130. H H H
 131. H H H
 132. H H H
 133. H H H
 134. H H H
 135. H H H
 136. H H H
 137. H H H
 138. H H H
 139. H H H
 140. H H H
 141. H H H
 142. H H H
 143. H H H
 144. H H H
 145. H H H
 146. H H H
 147. H H H
 148. H H H
 149. H H H
 150. H H H
 151. H H H
 152. H H H
 153. H H CD₃
 154. H H CD₃
 155. H H CD₃
 156. H H CD₃
 157. H H CD₃
 158. H H CD₃
 159. H H CD₃
 160. H H CD₃
 161. H H H
 162. H H H
 163. H H H
 164. H H H
 165. H H CD₃
 166. H H CD₃
 167. H H CD₃
 168. H H CD₃
 169. H H H
 170. H H H
 171. H H H
 172. H H H
 173. H H H
 174. H H H
 175. H H H
 176. H H H
 177. H H H
 178. H H H
 179. H H H
 180. H H H
 181. H H H
 182. H H H
 183. H H H
 184. H H H
 185. H H H
 186. H H H
 187. H H H
 188. H H H
 189. H H H
 190. H H H
 191. H H H
 192. H H H
 193. H H H
 194. H H H
 195. H H H
 196. H H H
 197. H H H
 198. H H H
 199. H H H
 200. H H H
 201.

H H
 202.

H H
 203.

H H
 204.

H H
 205.

H H
 206.

H H
 207.

H H
 208.

H H
 209.

H H
 210.

H H
 211.

H H
 212.

H H
 213.

H H
 214.

H H
 215.

H H
 216.

H H
 217. H

H
 218. H

H
 219. H

H
 220. H

H
 221. H

H
 222. H

H
 223. H

H
 224. H

H
 225. H

H
 226. H

H
 227. H

H
 228. H

H
 229. H

H
 230. H

H
 231. H

H
 232. H

H
 233. H H


234. H H


235. H H


236. H H


237. H H


238. H H


239. H H


240. H H


241. H H


242. H H


243. H H


244. H H


245. H H


246. H H


247. H H


248. H H


18. The composition of claim 17, wherein the compound is Compound x selected from the group consisting of Compound 1 through Compound 212,040; where Compound x has the formula Ir(L_(i) ¹)(L_(j) ²)₂; wherein x=248j+i−248, i is an integer from 1 to 248, and j is an integer from 1 to 855; wherein L_(j) ² is listed in the following table based on the following structure:

L² _(j), j R^(B1) R^(B2) R^(B3) R^(B4)
 1. H H H H
 2. CH₃ H H H
 3. H CH₃ H H
 4. H H CH₃ H
 5. H H H CH₃
 6. CH₃ H CH₃ H
 7. CH₃ H H CH₃
 8. H CH₃ CH₃ H
 9. H CH₃ H CH₃
 10. H H CH₃ CH₃
 11. CH₃ CH₃ CH₃ H
 12. CH₃ CH₃ H CH₃
 13. CH₃ H CH₃ CH₃
 14. H CH₃ CH₃ CH₃
 15. CH₃ CH₃ CH₃ CH₃
 16. CH₂CH₃ H H H
 17. CH₂CH₃ CH₃ H H
 18. CH₂CH₃ H CH₃ H
 19. CH₂CH₃ H H CH₃
 20. CH₂CH₃ CH₃ CH₃ H
 21. CH₂CH₃ CH₃ H CH₃
 22. CH₂CH₃ H CH₃ CH₃
 23. CH₂CH₃ CH₃ CH₃ CH₃
 24. H CH₂CH₃ H H
 25. CH₃ CH₂CH₃ H H
 26. H CH₂CH₃ CH₃ H
 27. H CH₂CH₃ H CH₃
 28. CH₃ CH₂CH₃ CH₃ H
 29. CH₃ CH₂CH₃ H CH₃
 30. H CH₂CH₃ CH₃ CH₃
 31. CH₃ CH₂CH₃ CH₃ CH₃
 32. H H CH₂CH₃ H
 33. CH₃ H CH₂CH₃ H
 34. H CH₃ CH₂CH₃ H
 35. H H CH₂CH₃ CH₃
 36. CH₃ CH₃ CH₂CH₃ H
 37. CH₃ H CH₂CH₃ CH₃
 38. H CH₃ CH₂CH₃ CH₃
 39. CH₃ CH₃ CH₂CH₃ CH₃
 40. CH(CH₃)₂ H H H
 41. CH(CH₃)₂ CH₃ H H
 42. CH(CH₃)₂ H CH₃ H
 43. CH(CH₃)₂ H H CH₃
 44. CH(CH₃)₂ CH₃ CH₃ H
 45. CH(CH₃)₂ CH₃ H CH₃
 46. CH(CH₃)₂ H CH₃ CH₃
 47. CH(CH₃)₂ CH₃ CH₃ CH₃
 48. H CH(CH₃)₂ H H
 49. CH₃ CH(CH₃)₂ H H
 50. H CH(CH₃)₂ CH₃ H
 51. H CH(CH₃)₂ H CH₃
 52. CH₃ CH(CH₃)₂ CH₃ H
 53. CH₃ CH(CH₃)₂ H CH₃
 54. H CH(CH₃)₂ CH₃ CH₃
 55. CH₃ CH(CH₃)₂ CH₃ CH₃
 56. H H CH(CH₃)₂ H
 57. CH₃ H CH(CH₃)₂ H
 58. H CH₃ CH(CH₃)₂ H
 59. H H CH(CH₃)₂ CH₃
 60. CH₃ CH₃ CH(CH₃)₂ H
 61. CH₃ H CH(CH₃)₂ CH₃
 62. H CH₃ CH(CH₃)₂ CH₃
 63. CH₃ CH₃ CH(CH₃)₂ CH₃
 64. CH₂CH(CH₃)₂ H H H
 65. CH₂CH(CH₃)₂ CH₃ H H
 66. CH₂CH(CH₃)₂ H CH₃ H
 67. CH₂CH(CH₃)₂ H H CH₃
 68. CH₂CH(CH₃)₂ CH₃ CH₃ H
 69. CH₂CH(CH₃)₂ CH₃ H CH₃
 70. CH₂CH(CH₃)₂ H CH₃ CH₃
 71. CH₂CH(CH₃)₂ CH₃ CH₃ CH₃
 72. H CH₂CH(CH₃)₂ H H
 73. CH₃ CH₂CH(CH₃)₂ H H
 74. H CH₂CH(CH₃)₂ CH₃ H
 75. H CH₂CH(CH₃)₂ H CH₃
 76. CH₃ CH₂CH(CH₃)₂ CH₃ H
 77. CH₃ CH₂CH(CH₃)₂ H CH₃
 78. H CH₂CH(CH₃)₂ CH₃ CH₃
 79. CH₃ CH₂CH(CH₃)₂ CH₃ CH₃
 80. H H CH₂CH(CH₃)₂ H
 81. CH₃ H CH₂CH(CH₃)₂ H
 82. H CH₃ CH₂CH(CH₃)₂ H
 83. H H CH₂CH(CH₃)₂ CH₃
 84. CH₃ CH₃ CH₂CH(CH₃)₂ H
 85. CH₃ H CH₂CH(CH₃)₂ CH₃
 86. H CH₃ CH₂CH(CH₃)₂ CH₃
 87. CH₃ CH₃ CH₂CH(CH₃)₂ CH₃
 88. C(CH₃)₃ H H H
 89. C(CH₃)₃ CH₃ H H
 90. C(CH₃)₃ H CH₃ H
 91. C(CH₃)₃ H H CH₃
 92. C(CH₃)₃ CH₃ CH₃ H
 93. C(CH₃)₃ CH₃ H CH₃
 94. C(CH₃)₃ H CH₃ CH₃
 95. C(CH₃)₃ CH₃ CH₃ CH₃
 96. H C(CH₃)₃ H H
 97. CH₃ C(CH₃)₃ H H
 98. H C(CH₃)₃ CH₃ H
 99. H C(CH₃)₃ H CH₃
 100. CH₃ C(CH₃)₃ CH₃ H
 101. CH₃ C(CH₃)₃ H CH₃
 102. H C(CH₃)₃ CH₃ CH₃
 103. CH₃ C(CH₃)₃ CH₃ CH₃
 104. H H C(CH₃)₃ H
 105. CH₃ H C(CH₃)₃ H
 106. H CH₃ C(CH₃)₃ H
 107. H H C(CH₃)₃ CH₃
 108. CH₃ CH₃ C(CH₃)₃ H
 109. CH₃ H C(CH₃)₃ CH₃
 110. H CH₃ C(CH₃)₃ CH₃
 111. CH₃ CH₃ C(CH₃)₃ CH₃
 112. CH₂C(CH₃)₃ H H H
 113. CH₂C(CH₃)₃ CH₃ H H
 114. CH₂C(CH₃)₃ H CH₃ H
 115. CH₂C(CH₃)₃ H H CH₃
 116. CH₂C(CH₃)₃ CH₃ CH₃ H
 117. CH₂C(CH₃)₃ CH₃ H CH₃
 118. CH₂C(CH₃)₃ H CH₃ CH₃
 119. CH₂C(CH₃)₃ CH₃ CH₃ CH₃
 120. H CH₂C(CH₃)₃ H H
 121. CH₃ CH₂C(CH₃)₃ H H
 122. H CH₂C(CH₃)₃ CH₃ H
 123. H CH₂C(CH₃)₃ H CH₃
 124. CH₃ CH₂C(CH₃)₃ CH₃ H
 125. CH₃ CH₂C(CH₃)₃ H CH₃
 126. H CH₂C(CH₃)₃ CH₃ CH₃
 127. CH₃ CH₂C(CH₃)₃ CH₃ CH₃
 128. H H CH₂C(CH₃)₃ H
 129. CH₃ H CH₂C(CH₃)₃ H
 130. H CH₃ CH₂C(CH₃)₃ H
 131. H H CH₂C(CH₃)₃ CH₃
 132. CH₃ CH₃ CH₂C(CH₃)₃ H
 133. CH₃ H CH₂C(CH₃)₃ CH₃
 134. H CH₃ CH₂C(CH₃)₃ CH₃
 135. CH₃ CH₃ CH₂C(CH₃)₃ CH₃
 136. CH₂C(CH₃)₂CF₃ H H H
 137. CH₂C(CH₃)₂CF₃ CH₃ H H
 138. CH₂C(CH₃)₂CF₃ H CH₃ H
 139. CH₂C(CH₃)₂CF₃ H H CH₃
 140. CH₂C(CH₃)₂CF₃ CH₃ CH₃ H
 141. CH₂C(CH₃)₂CF₃ CH₃ H CH₃
 142. CH₂C(CH₃)₂CF₃ H CH₃ CH₃
 143. CH₂C(CH₃)₂CF₃ CH₃ CH₃ CH₃
 144. H CH₂C(CH₃)₂CF₃ H H
 145. CH₃ CH₂C(CH₃)₂CF₃ H H
 146. H CH₂C(CH₃)₂CF₃ CH₃ H
 147. H CH₂C(CH₃)₂CF₃ H CH₃
 148. CH₃ CH₂C(CH₃)₂CF₃ CH₃ H
 149. CH₃ CH₂C(CH₃)₂CF₃ H CH₃
 150. H CH₂C(CH₃)₂CF₃ CH₃ CH₃
 151. CH₃ CH₂C(CH₃)₂CF₃ CH₃ CH₃
 152. H H CH₂C(CH₃)₂CF₃ H
 153. CH₃ H CH₂C(CH₃)₂CF₃ H
 154. H CH₃ CH₂C(CH₃)₂CF₃ H
 155. H H CH₂C(CH₃)₂CF₃ CH₃
 156. CH₃ CH₃ CH₂C(CH₃)₂CF₃ H
 157. CH₃ H CH₂C(CH₃)₂CF₃ CH₃
 158. H CH₃ CH₂C(CH₃)₂CF₃ CH₃
 159. CH₃ CH₃ CH₂C(CH₃)₂CF₃ CH₃
 160. CH₂CH₂CF₃ H H H
 161. CH₂CH₂CF₃ CH₃ H H
 162. CH₂CH₂CF₃ H CH₃ H
 163. CH₂CH₂CF₃ H H CH₃
 164. CH₂CH₂CF₃ CH₃ CH₃ H
 165. CH₂CH₂CF₃ CH₃ H CH₃
 166. CH₂CH₂CF₃ H CH₃ CH₃
 167. CH₂CH₂CF₃ CH₃ CH₃ CH₃
 168. H CH₂CH₂CF₃ H H
 169. CH₃ CH₂CH₂CF₃ H H
 170. H CH₂CH₂CF₃ CH₃ H
 171. H CH₂CH₂CF₃ H CH₃
 172. CH₃ CH₂CH₂CF₃ CH₃ H
 173. CH₃ CH₂CH₂CF₃ H CH₃
 174. H CH₂CH₂CF₃ CH₃ CH₃
 175. CH₃ CH₂CH₂CF₃ CH₃ CH₃
 176. H H CH₂CH₂CF₃ H
 177. CH₃ H CH₂CH₂CF₃ H
 178. H CH₃ CH₂CH₂CF₃ H
 179. H H CH₂CH₂CF₃ CH₃
 180. CH₃ CH₃ CH₂CH₂CF₃ H
 181. CH₃ H CH₂CH₂CF₃ CH₃
 182. H CH₃ CH₂CH₂CF₃ CH₃
 183. CH₃ CH₃ CH₂CH₂CF₃ CH₃
 184.

H H H
 185.

CH₃ H H
 186.

H CH₃ H
 187.

H H CH₃
 188.

CH₃ CH₃ H
 189.

CH₃ H CH₃
 190.

H CH₃ CH₃
 191.

CH₃ CH₃ CH₃
 192. H

H H
 193. CH₃

H H
 194. H

CH₃ H
 195. H

H CH₃
 196. CH₃

CH₃ H
 197. CH₃

H CH₃
 198. H

CH₃ CH₃
 199. CH₃

CH₃ CH₃
 200. H H

H
 201. CH₃ H

H
 202. H CH₃

H
 203. H H

CH₃
 204. CH₃ CH₃

H
 205. CH₃ H

CH₃
 206. H CH₃

CH₃
 207. CH₃ CH₃

CH₃
 208.

H H H
 209.

CH₃ H H
 210.

H CH₃ H
 211.

H H CH₃
 212.

CH₃ CH₃ H
 213.

CH₃ H CH₃
 214.

H CH₃ CH₃
 215.

CH₃ CH₃ CH₃
 216. H

H H
 217. CH₃

H H
 218. H

CH₃ H
 219. H

H CH₃
 220. CH₃

CH₃ H
 221. CH₃

H CH₃
 222. H

CH₃ CH₃
 223. CH₃

CH₃ CH₃
 224. H H

H
 225. CH₃ H

H
 226. H CH₃

H
 227. H H

CH₃
 228. CH₃ CH₃

H
 229. CH₃ H

CH₃
 230. H CH₃

CH₃
 231. CH₃ CH₃

CH₃
 232.

H H H
 233.

CH₃ H H
 234.

H CH₃ H
 235.

H H CH₃
 236.

CH₃ CH₃ H
 237.

CH₃ H CH₃
 238.

H CH₃ CH₃
 239.

CH₃ CH₃ CH₃
 240. H

H H
 241. CH₃

H H
 242. H

CH₃ H
 243. H

H CH₃
 244. CH₃

CH₃ H
 245. CH₃

H CH₃
 246. H

CH₃ CH₃
 247. CH₃

CH₃ CH₃
 248. H H

H
 249. CH₃ H

H
 250. H CH₃

H
 251. H H

CH₃
 252. CH₃ CH₃

H
 253. CH₃ H

CH₃
 254. H CH₃

CH₃
 255. CH₃ CH₃

CH₃
 256.

H H H
 257.

CH₃ H H
 258.

H CH₃ H
 259.

H H CH₃
 260.

CH₃ CH₃ H
 261.

CH₃ H CH₃
 262.

H CH₃ CH₃
 263.

CH₃ CH₃ CH₃
 264. H

H H
 265. CH₃

H H
 266. H

CH₃ H
 267. H

H CH₃
 268. CH₃

CH₃ H
 269. CH₃

H CH₃
 270. H

CH₃ CH₃
 271. CH₃

CH₃ CH₃
 272. H H

H
 273. CH₃ H

H
 274. H CH₃

H
 275. H H

CH₃
 276. CH₃ CH₃

H
 277. CH₃ H

CH₃
 278. H CH₃

CH₃
 279. CH₃ CH₃

CH₃
 280.

H H H
 281.

CH₃ H H
 282.

H CH₃ H
 283.

H H CH₃
 284.

CH₃ CH₃ H
 285.

CH₃ H CH₃
 286.

H CH₃ CH₃
 287.

CH₃ CH₃ CH₃
 288. H

H H
 289. CH₃

H H
 290. H

CH₃ H
 291. H

H CH₃
 292. CH₃

CH₃ H
 293. CH₃

H CH₃
 294. H

CH₃ CH₃
 295. CH₃

CH₃ CH₃
 296. H H

H
 297. CH₃ H

H
 298. H CH₃

H
 299. H H

CH₃
 300. CH₃ CH₃

H
 301. CH₃ H

CH₃
 302. H CH₃

CH₃
 303. CH₃ CH₃

CH₃
 304.

H H H
 305.

CH₃ H H
 306.

H CH₃ H
 307.

H H CH₃
 308.

CH₃ CH₃ H
 309.

CH₃ H CH₃
 310.

H CH₃ CH₃
 311.

CH₃ CH₃ CH₃
 312. H

H H
 313. CH₃

H H
 314. H

CH₃ H
 315. H

H CH₃
 316. CH₃

CH₃ H
 317. CH₃

H CH₃
 318. H

CH₃ CH₃
 319. CH₃

CH₃ CH₃
 320. H H

H
 321. CH₃ H

H
 322. H CH₃

H
 323. H H

CH₃
 324. CH₃ CH₃

H
 325. CH₃ H

CH₃
 326. H CH₃

CH₃
 327. CH₃ CH₃

CH₃
 328. CH(CH₃)₂ H CH₂CH₃ H
 329. CH(CH₃)₂ H CH(CH₃)₂ H
 330. CH(CH₃)₂ H CH₂CH(CH₃)₂ H
 331. CH(CH₃)₂ H C(CH₃)₃ H
 332. CH(CH₃)₂ H CH₂C(CH₃)₃ H
 333. CH(CH₃)₂ H CH₂CH₂CF₃ H
 334. CH(CH₃)₂ H CH₂C(CH₃)₂CF₃ H
 335. CH(CH₃)₂ H

H
 336. CH(CH₃)₂ H

H
 337. CH(CH₃)₂ H

H
 338. CH(CH₃)₂ H

H
 339. CH(CH₃)₂ H

H
 340. CH(CH₃)₂ H

H
 341. C(CH₃)₃ H CH₂CH₃ H
 342. C(CH₃)₃ H CH(CH₃)₂ H
 343. C(CH₃)₃ H CH₂CH(CH₃)₂ H
 344. C(CH₃)₃ H C(CH₃)₃ H
 345. C(CH₃)₃ H CH₂C(CH₃)₃ H
 346. C(CH₃)₃ H CH₂CH₂CF₃ H
 347. C(CH₃)₃ H CH₂C(CH₃)₂CF₃ H
 348. C(CH₃)₃ H

H
 349. C(CH₃)₃ H

H
 350. C(CH₃)₃ H

H
 351. C(CH₃)₃ H

H
 352. C(CH₃)₃ H

H
 353. C(CH₃)₃ H

H
 354. CH₂C(CH₃)₃ H CH₂CH₃ H
 355. CH₂C(CH₃)₃ H CH(CH₃)₂ H
 356. CH₂C(CH₃)₃ H CH₂CH(CH₃)₂ H
 357. CH₂C(CH₃)₃ H C(CH₃)₃ H
 358. CH₂C(CH₃)₃ H CH₂C(CH₃)₃ H
 359. CH₂C(CH₃)₃ H CH₂CH₂CF₃ H
 360. CH₂C(CH₃)₃ H CH₂C(CH₃)₂CF₃ H
 361. CH₂C(CH₃)₃ H

H
 362. CH₂C(CH₃)₃ H

H
 363. CH₂C(CH₃)₃ H

H
 364. CH₂C(CH₃)₃ H

H
 365. CH₂C(CH₃)₃ H

H
 366. CH₂C(CH₃)₃ H

H
 367.

H CH₂CH₃ H
 368.

H CH(CH₃)₂ H
 369.

H CH₂CH(CH₃)₂ H
 370.

H C(CH₃)₃ H
 371.

H CH₂C(CH₃)₃ H
 372.

H CH₂CH₂CF₃ H
 373.

H CH₂C(CH₃)₂CF₃ H
 374.

H

H
 375.

H

H
 376.

H

H
 377.

H

H
 378.

H

H
 379.

H

H
 380.

H CH₂CH₃ H
 381.

H CH(CH₃)₂ H
 382.

H CH₂CH(CH₃)₂ H
 383.

H C(CH₃)₃ H
 384.

H CH₂C(CH₃)₃ H
 385.

H CH₂CH₂CF₃ H
 386.

H CH₂C(CH₃)₂CF₃ H
 387.

H

H
 388.

H

H
 389.

H

H
 390.

H

H
 391.

H

H
 392.

H

H
 393.

H CH₂CH(CH₃)₂ H
 394.

H C(CH₃)₃ H
 395.

H CH₂C(CH₃)₃ H
 396.

H CH₂CH₂CF₃ H
 397.

H CH₂C(CH₃)₂CF₃ H
 398.

H

H
 399.

H

H
 400.

H

H
 401.

H

H
 402.

H

H
 403.

H

H
 404.

H CH₂CH(CH₃)₂ H
 405.

H C(CH₃)₃ H
 406.

H CH₂C(CH₃)₃ H
 407.

H CH₂CH₂CF₃ H
 408.

H CH₂C(CH₃)₂CF₃ H
 409.

H

H
 410.

H

H
 411.

H

H
 412.

H

H
 413.

H

H
 414.

H

H
 415.

H CH₂CH(CH₃)₂ H
 416.

H C(CH₃)₃ H
 417.

H CH₂C(CH₃)₃ H
 418.

H CH₂CH₂CF₃ H
 419.

H CH₂C(CH₃)₂CF₃ H
 420.

H

H
 421.

H

H
 422.

H

H
 423.

H

H
 424.

H

H
 425.

H

H
 426. CD₃ H H H
 427. H CD₃ H H
 428. H H CD₃ H
 429. H H H CD₃
 430. CD₃ H CD₃ H
 431. CD₃ H H CD₃
 432. H CD₃ CD₃ H
 433. H CD₃ H CD₃
 434. H H CD₃ CD₃
 435. CD₃ CD₃ CD₃ H
 436. CD₃ CD₃ H CD₃
 437. CD₃ H CD₃ CD₃
 438. H CD₃ CD₃ CD₃
 439. CD₃ CD₃ CD₃ CD₃
 440. CD₂CH₃ H H H
 441. CD₂CH₃ CD₃ H H
 442. CD₂CH₃ H CD₃ H
 443. CD₂CH₃ H H CD₃
 444. CD₂CH₃ CD₃ CD₃ H
 445. CD₂CH₃ CD₃ H CD₃
 446. CD₂CH₃ H CD₃ CD₃
 447. CD₂CH₃ CD₃ CD₃ CD₃
 448. H CD₂CH₃ H H
 449. CD₃ CD₂CH₃ H H
 450. H CD₂CH₃ CD₃ H
 451. H CD₂CH₃ H CD₃
 452. CD₃ CD₂CH₃ CD₃ H
 453. CD₃ CD₂CH₃ H CD₃
 454. H CD₂CH₃ CD₃ CD₃
 455. CD₃ CD₂CH₃ CD₃ CD₃
 456. H H CD₂CH₃ H
 457. CD₃ H CD₂CH₃ H
 458. H CD₃ CD₂CH₃ H
 459. H H CD₂CH₃ CD₃
 460. CD₃ CD₃ CD₂CH₃ H
 461. CD₃ H CD₂CH₃ CD₃
 462. H CD₃ CD₂CH₃ CD₃
 463. CD₃ CD₃ CD₂CH₃ CD₃
 464. CD(CH₃)₂ H H H
 465. CD(CH₃)₂ CD₃ H H
 466. CD(CH₃)₂ H CD₃ H
 467. CD(CH₃)₂ H H CD₃
 468. CD(CH₃)₂ CD₃ CD₃ H
 469. CD(CH₃)₂ CD₃ H CD₃
 470. CD(CH₃)₂ H CD₃ CD₃
 471. CD(CH₃)₂ CD₃ CD₃ CD₃
 472. H CD(CH₃)₂ H H
 473. CD₃ CD(CH₃)₂ H H
 474. H CD(CH₃)₂ CD₃ H
 475. H CD(CH₃)₂ H CD₃
 476. CD₃ CD(CH₃)₂ CD₃ H
 477. CD₃ CD(CH₃)₂ H CD₃
 478. H CD(CH₃)₂ CD₃ CD₃
 479. CD₃ CD(CH₃)₂ CD₃ CD₃
 480. H H CD(CH₃)₂ H
 481. CD₃ H CD(CH₃)₂ H
 482. H CD₃ CD(CH₃)₂ H
 483. H H CD(CH₃)₂ CD₃
 484. CD₃ CD₃ CD(CH₃)₂ H
 485. CD₃ H CD(CH₃)₂ CD₃
 486. H CD₃ CD(CH₃)₂ CD₃
 487. CD₃ CD₃ CD(CH₃)₂ CD₃
 488. CD(CD₃)₂ H H H
 489. CD(CD₃)₂ CD₃ H H
 490. CD(CD₃)₂ H CD₃ H
 491. CD(CD₃)₂ H H CD₃
 492. CD(CD₃)₂ CD₃ CD₃ H
 493. CD(CD₃)₂ CD₃ H CD₃
 494. CD(CD₃)₂ H CD₃ CD₃
 495. CD(CD₃)₂ CD₃ CD₃ CD₃
 496. H CD(CD₃)₂ H H
 497. CD₃ CD(CD₃)₂ H H
 498. H CD(CD₃)₂ CD₃ H
 499. H CD(CD₃)₂ H CD₃
 500. CD₃ CD(CD₃)₂ CD₃ H
 501. CD₃ CD(CD₃)₂ H CD₃
 502. H CD(CD₃)₂ CD₃ CD₃
 503. CD₃ CD(CD₃)₂ CD₃ CD₃
 504. H H CD(CD₃)₂ H
 505. CD₃ H CD(CD₃)₂ H
 506. H CD₃ CD(CD₃)₂ H
 507. H H CD(CD₃)₂ CD₃
 508. CD₃ CD₃ CD(CD₃)₂ H
 509. CD₃ H CD(CD₃)₂ CD₃
 510. H CD₃ CD(CD₃)₂ CD₃
 511. CD₃ CD₃ CD(CD₃)₂ CD₃
 512. CD₂CH(CH₃)₂ H H H
 513. CD₂CH(CH₃)₂ CD₃ H H
 514. CD₂CH(CH₃)₂ H CD₃ H
 515. CD₂CH(CH₃)₂ H H CD₃
 516. CD₂CH(CH₃)₂ CD₃ CD₃ H
 517. CD₂CH(CH₃)₂ CD₃ H CD₃
 518. CD₂CH(CH₃)₂ H CD₃ CD₃
 519. CD₂CH(CH₃)₂ CD₃ CD₃ CD₃
 520. H CD₂CH(CH₃)₂ H H
 521. CD₃ CD₂CH(CH₃)₂ H H
 522. H CD₂CH(CH₃)₂ CD₃ H
 523. H CD₂CH(CH₃)₂ H CD₃
 524. CD₃ CD₂CH(CH₃)₂ CD₃ H
 525. CD₃ CD₂CH(CH₃)₂ H CD₃
 526. H CD₂CH(CH₃)₂ CD₃ CD₃
 527. CD₃ CD₂CH(CH₃)₂ CD₃ CD₃
 528. H H CD₂CH(CH₃)₂ H
 529. CD₃ H CD₂CH(CH₃)₂ H
 530. H CD₃ CD₂CH(CH₃)₂ H
 531. H H CD₂CH(CH₃)₂ CD₃
 532. CD₃ CD₃ CD₂CH(CH₃)₂ H
 533. CD₃ H CD₂CH(CH₃)₂ CD₃
 534. H CD₃ CD₂CH(CH₃)₂ CD₃
 535. CD₃ CD₃ CD₂CH(CH₃)₂ CD₃
 536. CD₂C(CH₃)₃ H H H
 537. CD₂C(CH₃)₃ CD₃ H H
 538. CD₂C(CH₃)₃ H CD₃ H
 539. CD₂C(CH₃)₃ H H CD₃
 540. CD₂C(CH₃)₃ CD₃ CD₃ H
 541. CD₂C(CH₃)₃ CD₃ H CD₃
 542. CD₂C(CH₃)₃ H CD₃ CD₃
 543. CD₂C(CH₃)₃ CH₃ CD₃ CD₃
 544. H CD₂C(CH₃)₃ H H
 545. CD₃ CD₂C(CH₃)₃ H H
 546. H CD₂C(CH₃)₃ CD₃ H
 547. H CD₂C(CH₃)₃ H CD₃
 548. CD₃ CD₂C(CH₃)₃ CD₃ H
 549. CD₃ CD₂C(CH₃)₃ H CD₃
 550. H CD₂C(CH₃)₃ CD₃ CD₃
 551. CD₃ CD₂C(CH₃)₃ CD₃ CD₃
 552. H H CD₂C(CH₃)₃ H
 553. CD₃ H CD₂C(CH₃)₃ H
 554. H CD₃ CD₂C(CH₃)₃ H
 555. H H CD₂C(CH₃)₃ CD₃
 556. CD₃ CD₃ CD₂C(CH₃)₃ H
 557. CD₃ H CD₂C(CH₃)₃ CD₃
 558. H CD₃ CD₂C(CH₃)₃ CD₃
 559. CD₃ CD₃ CD₂C(CH₃)₃ CD₃
 560. CD₂C(CH₃)₂CF₃ H H H
 561. CD₂C(CH₃)₂CF₃ CD₃ H H
 562. CD₂C(CH₃)₂CF₃ H CD₃ H
 563. CD₂C(CH₃)₂CF₃ H H CD₃
 564. CD₂C(CH₃)₂CF₃ CD₃ CD₃ H
 565. CD₂C(CH₃)₂CF₃ CD₃ H CD₃
 566. CD₂C(CH₃)₂CF₃ H CD₃ CD₃
 567. CD₂C(CH₃)₂CF₃ CD₃ CD₃ CD₃
 568. H CD₂C(CH₃)₂CF₃ H H
 569. CD₃ CD₂C(CH₃)₂CF₃ H H
 570. H CD₂C(CH₃)₂CF₃ CD₃ H
 571. H CD₂C(CH₃)₂CF₃ H CD₃
 572. CD₃ CD₂C(CH₃)₂CF₃ CD₃ H
 573. CD₃ CD₂C(CH₃)₂CF₃ H CD₃
 574. H CD₂C(CH₃)₂CF₃ CD₃ CD₃
 575. CD₃ CD₂C(CH₃)₂CF₃ CD₃ CD₃
 576. H H CD₂C(CH₃)₂CF₃ H
 577. CD₃ H CD₂C(CH₃)₂CF₃ H
 578. H CD₃ CD₂C(CH₃)₂CF₃ H
 579. H H CD₂C(CH₃)₂CF₃ CD₃
 580. CD₃ CD₃ CD₂C(CH₃)₂CF₃ H
 581. CD₃ H CD₂C(CH₃)₂CF₃ CD₃
 582. H CD₃ CD₂C(CH₃)₂CF₃ CD₃
 583. CD₃ CD₃ CD₂C(CH₃)₂CF₃ CD₃
 584. CD₂CH₂CF₃ H H H
 585. CD₂CH₂CF₃ CD₃ H H
 586. CD₂CH₂CF₃ H CD₃ H
 587. CD₂CH₂CF₃ H H CD₃
 588. CD₂CH₂CF₃ CD₃ CD₃ H
 589. CD₂CH₂CF₃ CD₃ H CD₃
 590. CD₂CH₂CF₃ H CD₃ CD₃
 591. CD₂CH₂CF₃ CD₃ CD₃ CD₃
 592. H CD₂CH₂CF₃ H H
 593. CD₃ CD₂CH₂CF₃ H H
 594. H CD₂CH₂CF₃ CD₃ H
 595. H CD₂CH₂CF₃ H CD₃
 596. CD₃ CD₂CH₂CF₃ CD₃ H
 597. CD₃ CD₂CH₂CF₃ H CD₃
 598. H CD₂CH₂CF₃ CD₃ CD₃
 599. CD₃ CD₂CH₂CF₃ CD₃ CD₃
 600. H H CD₂CH₂CF₃ H
 601. CD₃ H CD₂CH₂CF₃ H
 602. H CD₃ CD₂CH₂CF₃ H
 603. H H CD₂CH₂CF₃ CD₃
 604. CD₃ CD₃ CD₂CH₂CF₃ H
 605. CD₃ H CD₂CH₂CF₃ CD₃
 606. H CD₃ CD₂CH₂CF₃ CD₃
 607. CD₃ CD₃ CD₂CH₂CF₃ CD₃
 608.

H H H
 609.

CD₃ H H
 610.

H CD₃ H
 611.

H H CD₃
 612.

CD₃ CD₃ H
 613.

CD₃ H CD₃
 614.

H CD₃ CD₃
 615.

CD₃ CD₃ CD₃
 616. H

H H
 617. CD₃

H H
 618. H

CD₃ H
 619. H

H CD₃
 620. CD₃

CD₃ H
 621. CD₃

H CD₃
 622. H

CD₃ CD₃
 623. CD₃

CD₃ CD₃
 624. H H

H
 625. CD₃ H

H
 626. H CD₃

H
 627. H H

CD₃
 628. CD₃ CD₃

H
 629. CD₃ H

CD₃
 630. H CD₃

CD₃
 631. CD₃ CD₃

CD₃
 632.

H H H
 633.

CD₃ H H
 634.

H CD₃ H
 635.

H H CD₃
 636.

CD₃ CD₃ H
 637.

CD₃ H CD₃
 638.

H CD₃ CD₃
 639.

CD₃ CD₃ CD₃
 640. H

H H
 641. CD₃

H H
 642. H

CD₃ H
 643. H

H CD₃
 644. CD₃

CD₃ H
 645. CD₃

H CD₃
 646. H

CD₃ CD₃
 647. CH₃

CD₃ CD₃
 648. H H

H
 649. CD₃ H

H
 650. H CD₃

H
 651. H H

CD₃
 652. CD₃ CD₃

H
 653. CD₃ H

CD₃
 654. H CD₃

CD₃
 655. CD₃ CD₃

CD₃
 656.

H H H
 657.

CD₃ H H
 658.

H CD₃ H
 659.

H H CD₃
 660.

CD₃ CD₃ H
 661.

CD₃ H CD₃
 662.

H CD₃ CD₃
 663.

CD₃ CD₃ CD₃
 664. H

H H
 665. CD₃

H H
 666. H

CD₃ H
 667. H

H CD₃
 668. CD₃

CD₃ H
 669. CD₃

H CD₃
 670. H

CD₃ CD₃
 671. CD₃

CD₃ CD₃
 672. H H

H
 673. CD₃ H

H
 674. H CD₃

H
 675. H H

CD₃
 676. CD₃ CD₃

H
 677. CD₃ H

CD₃
 678. H CD₃

CD₃
 679. CD₃ CD₃

CD₃
 680.

H H H
 681.

CD₃ H H
 682.

H CD₃ H
 683.

H H CD₃
 684.

CD₃ CD₃ H
 685.

CD₃ H CD₃
 686.

H CD₃ CD₃
 687.

CD₃ CD₃ CD₃
 688. H

H H
 689. CD₃

H H
 690. H

CD₃ H
 691. H

H CD₃
 692. CD₃

CD₃ H
 693. CD₃

H CD₃
 694. H

CD₃ CD₃
 695. CD₃

CD₃ CD₃
 696. H H

H
 697. CD₃ H

H
 698. H CD₃

H
 699. H H

CD₃
 700. CD₃ CD₃

H
 701. CD₃ H

CD₃
 702. H CD₃

CD₃
 703. CD₃ CD₃

CD₃
 704.

H H H
 705.

CD₃ H H
 706.

H CD₃ H
 707.

H H CD₃
 708.

CD₃ CD₃ H
 709.

CD₃ H CD₃
 710.

H CD₃ CD₃
 711.

CD₃ CD₃ CD₃
 712. H

H H
 713. CD₃

H H
 714. H

CD₃ H
 715. H

H CD₃
 716. CD₃

CD₃ H
 717. CD₃

H CD₃
 718. H

CD₃ CD₃
 719. CD₃

CD₃ CD₃
 720. H H

H
 721. CD₃ H

H
 722. H CD₃

H
 723. H H

CD₃
 724. CD₃ CD₃

H
 725. CD₃ H

CD₃
 726. H CD₃

CD₃
 727. CD₃ CD₃

CD₃
 728.

H H H
 729.

CD₃ H H
 730.

H CD₃ H
 731.

H H CD₃
 732.

CH₃ CH₃ H
 733.

CD₃ H CD₃
 734.

H CD₃ CD₃
 735.

CD₃ CD₃ CD₃
 736. H

H H
 737. CD₃

H H
 738. H

CD₃ H
 739. H

H CD₃
 740. CD₃

CD₃ H
 741. CD₃

H CD₃
 742. H

CD₃ CD₃
 743. CD₃

CD₃ CD₃
 744. H H

H
 745. CD₃ H

H
 746. H CD₃

H
 747. H H

CD₃
 748. CD₃ CD₃

H
 749. CD₃ H

CD₃
 750. H CD₃

CD₃
 751. CD₃ CD₃

CD₃
 752. CD(CH₃)₂ H CD₂CH₃ H
 753. CD(CH₃)₂ H CD(CH₃)₂ H
 754. CD(CH₃)₂ H CD₂CH(CH₃)₂ H
 755. CD(CH₃)₂ H C(CH₃)₃ H
 756. CD(CH₃)₂ H CD₂C(CH₃)₃ H
 757. CD(CH₃)₂ H CD₂CH₂CF₃ H
 758. CD(CH₃)₂ H CD₂C(CH₃)₂CF₃ H
 759. CD(CH₃)₂ H

H
 760. CD(CH₃)₂ H

H
 761. CD(CH₃)₂ H

H
 762. CD(CH₃)₂ H

H
 763. CD(CH₃)₂ H

H
 764. CD(CH₃)₂ H

H
 765. C(CH₃)₃ H CD₂CH₃ H
 766. C(CH₃)₃ H CD(CH₃)₂ H
 767. C(CH₃)₃ H CD₂CH(CH₃)₂ H
 768. C(CH₃)₃ H C(CH₃)₃ H
 769. C(CH₃)₃ H CD₂C(CH₃)₃ H
 770. C(CH₃)₃ H CD₂CH₂CF₃ H
 771. C(CH₃)₃ H CD₂C(CH₃)₂CF₃ H
 772. C(CH₃)₃ H

H
 773. C(CH₃)₃ H

H
 774. C(CH₃)₃ H

H
 775. C(CH₃)₃ H

H
 776. C(CH₃)₃ H

H
 777. C(CH₃)₃ H

H
 778. CD₂C(CH₃)₃ H CD₂CH₃ H
 779. CD₂C(CH₃)₃ H CD(CH₃)₂ H
 780. CD₂C(CH₃)₃ H CD₂CH(CH₃)₂ H
 781. CD₂C(CH₃)₃ H C(CH₃)₃ H
 782. CD₂C(CH₃)₃ H CD₂C(CH₃)₃ H
 783. CD₂C(CH₃)₃ H CD₂CH₂CF₃ H
 784. CD₂C(CH₃)₃ H CD₂C(CH₃)₂CF₃ H
 785. CD₂C(CH₃)₃ H

H
 786. CD₂C(CH₃)₃ H

H
 787. CD₂C(CH₃)₃ H

H
 788. CD₂C(CH₃)₃ H

H
 789. CD₂C(CH₃)₃ H

H
 790. CD₂C(CH₃)₃ H

H
 791.

H CD₂CH₃ H
 792.

H CD(CH₃)₂ H
 793.

H CD₂CH(CH₃)₂ H
 794.

H C(CH₃)₃ H
 795.

H CD₂C(CH₃)₃ H
 796.

H CD₂CH₂CF₃ H
 797.

H CD₂C(CH₃)₂CF₃ H
 798.

H

H
 799.

H

H
 800.

H

H
 801.

H

H
 802.

H

H
 803.

H

H
 804.

H CD₂CH₃ H
 805.

H CD(CH₃)₂ H
 806.

H CD₂CH(CH₃)₂ H
 807.

H C(CH₃)₃ H
 808.

H CD₂C(CH₃)₃ H
 809.

H CD₂CH₂CF₃ H
 810.

H CD₂C(CH₃)₂CF₃ H
 811.

H

H
 812.

H

H
 813.

H

H
 814.

H

H
 815.

H

H
 816.

H

H
 817.

H CD₂CH₃ H
 818.

H CD(CH₃)₂ H
 819.

H CD₂CH(CH₃)₂ H
 820.

H C(CH₃)₃ H
 821.

H CD₂C(CH₃)₃ H
 822.

H CD₂CH₂CF₃ H
 823.

H CD₂C(CH₃)₂CF₃ H
 824.

H

H
 825.

H

H
 826.

H

H
 827.

H

H
 828.

H

H
 829.

H

H
 830.

H CD₂CH₃ H
 831.

H CD(CH₃)₂ H
 832.

H CD₂CH(CH₃)₂ H
 833.

H C(CH₃)₃ H
 834.

H CD₂C(CH₃)₃ H
 835.

H CD₂CH₂CF₃ H
 836.

H CD₂C(CH₃)₂CF₃ H
 837.

H

H
 838.

H

H
 839.

H

H
 840.

H

H
 841.

H

H
 842.

H

H
 843.

H CD₂CH₃ H
 844.

H CD(CH₃)₂ H
 845.

H CD₂CH(CH₃)₂ H
 846.

H C(CH₃)₃ H
 847.

H CD₂C(CH₃)₃ H
 848.

H CD₂CH₂CF₃ H
 849.

H CD₂C(CH₃)₂CF₃ H
 850.

H

H
 851.

H

H
 852.

H

H
 853.

H

H
 854.

H

H
 855.

H

 H.


19. The composition of claim 1, wherein, in ligand L¹, at least one substituent R is single bonded to a ring selected from the group consisting of a phenyl ring, a pyridine ring, and a triazine ring. 